Synthesis of methyl 4,6- O-benzylidene-2,3-dideoxy-5-thio-β- dl- threo-hex-2-enopyranoside via hetero-Diels–Alder reaction and unusual stabilities of 1,5-anhydro-4,6- O-benzylidene 2,3-dideoxy-5-thio- dl- threo-hex-2-enitol

The title compound was prepared via hetero-Diels–Alder reaction of 1-acetoxy-1,3-butadiene and thioaldehyde, followed by Pummerer rearrangement. Different from the corresponding sugar and 5a-carba sugar, C-inside isomer of 1,5-anhydro-4,6- O-benzylidene-2,3-dideoxy-5-thio- dl- thero-hex-2-enitol was...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 65; no. 3; pp. 599 - 606
Main Authors Watanabe, Yuhya, Sakakibara, Tohru
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.01.2009
Elsevier
Subjects
5-Thiosugar
C-inside form
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Chemistry, Organic
Exact sciences and technology
Hetero-Diels–Alder reaction
Optical resolution
Organic chemistry
Physical Sciences
Preparations and properties
Pummerer rearrangement
Science & Technology
5-Thiosugar
Hetero-Diels–Alder reaction
Pummerer rearrangement
C-inside form
Optical resolution
Hetero-Diels-Alder reaction
Ab initio method
Pummerer reaction
Theoretical study
Oside
Thermodynamic stability
Organic sulfide
Thioaldehyde
Threo stereoisomer
Thioglycoside
Hetero Diels Alder reaction
Chemical synthesis
Online AccessGet full text

Cover

Abstract The title compound was prepared via hetero-Diels–Alder reaction of 1-acetoxy-1,3-butadiene and thioaldehyde, followed by Pummerer rearrangement. Different from the corresponding sugar and 5a-carba sugar, C-inside isomer of 1,5-anhydro-4,6- O-benzylidene-2,3-dideoxy-5-thio- dl- thero-hex-2-enitol was found to be thermodynamically more stable than the corresponding O-inside one and these thermodynamic stabilities were corroborated by ab initio calculations. [Display omitted]
AbstractList The title compound was prepared via hetero-Diels–Alder reaction of 1-acetoxy-1,3-butadiene and thioaldehyde, followed by Pummerer rearrangement. Different from the corresponding sugar and 5a-carba sugar, C-inside isomer of 1,5-anhydro-4,6- O-benzylidene-2,3-dideoxy-5-thio- dl- thero-hex-2-enitol was found to be thermodynamically more stable than the corresponding O-inside one and these thermodynamic stabilities were corroborated by ab initio calculations. [Display omitted]
The title compound was prepared via hetero-Diels-Alder reaction of 1-acetoxy-1,3-butadiene and thioaldehyde, followed by Pummerer rearrangement. Different from the corresponding sugar and 5a-carba sugar, C-inside isomer of 1,5-anhydro-4,6-O-benzylidene-2,3-dideoxy-5-thio-DL-thero-hex-2-enitol was found to be thermodynamically more stable than the corresponding O-inside one and these thermodynamic stabilities were corroborated by ab initio calculations. (c) 2008 Elsevier Ltd. All rights reserved.
Author Sakakibara, Tohru
Watanabe, Yuhya
Author_xml – sequence: 1
  givenname: Yuhya
  surname: Watanabe
  fullname: Watanabe, Yuhya
– sequence: 2
  givenname: Tohru
  surname: Sakakibara
  fullname: Sakakibara, Tohru
  email: baratoru@yokohama-cu.ac.jp
BackLink http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21047576$$DView record in Pascal Francis
BookMark eNqNkT9uFDEUhy0UJDaBA9C5oWK92J4Z2yuqaPkrRUoB1JbH80bjlWOvbG_IUHEHbsJBOEROgpeN0hAhqveK32f9nr9TdBJiAISeM7pilIlX21WBsuKUqhVjK8q7R2jBWtGSrmXiBC0obSlpKadP0GnOW0opY7xZoNtPcygTZJdxHPEVlGn2uF0Kgi9JD-Hb7N0AAQhfNmSoa7yZSUfK5CL59ZPgwRNcpgSRTHBDOIEQd3MyIeaaxdfO4AkKpEjeOPD59vuPcz9AwgmMLS4GbMKA92Gf98bjXEzvvCsO_nRhy46YMM1Dpf8uhB8o9EAbV6J_ih6Pxmd4djfP0Jd3bz9vPpCLy_cfN-cXxDZcFjI2cm0k77i0ksm246oXoFQHQhkYe7kehYKh47QZoefQW0Z7row0oNZCUN6cIXZ816aYc4JR75K7MmnWjOqDJL3VVZI-SNKM6SqpMi-OzM5ka_xYv866fA9yRlvZSVFzL4-5r9DHMVsHwcJ9rNrkgkvZKHpYa1r9f3rjijm42MR9KBV9fUSrLrh2kPQdPrgEtughun-c8xtqb8v1
CODEN TETRAB
CitedBy_id crossref_primary_10_1016_j_tet_2012_01_039
crossref_primary_10_1021_acs_orglett_8b01321
crossref_primary_10_1002_ejoc_201501538
crossref_primary_10_1007_s10593_014_1497_0
crossref_primary_10_1039_C7QO00786H
crossref_primary_10_1155_2013_813451
crossref_primary_10_1016_j_carres_2009_02_028
Cites_doi 10.1007/s00253-005-0156-x
10.1021/jm050595e
10.1016/j.tet.2004.06.006
10.1016/S0040-4039(03)00842-6
10.1016/j.tetlet.2007.09.056
10.1016/S0008-6215(98)00221-3
10.1021/ja00361a062
10.1039/p19920001261
10.1021/ie50480a063
10.1016/S0040-4020(01)90118-8
10.1016/S0040-4039(00)72232-5
10.1246/bcsj.56.270
10.1016/S0040-4020(98)00848-5
10.1039/c39870001200
10.1002/ejoc.200300334
10.1021/jo00418a001
10.1039/C39870001836
10.1021/jo00359a034
10.1021/jo00838a023
10.1002/cber.19100430241
10.1016/S0008-6215(00)00052-5
10.1021/jo00355a018
10.1016/S0040-4020(97)10096-5
10.1016/0008-6215(83)88230-5
ContentType Journal Article
Copyright 2008 Elsevier Ltd
2009 INIST-CNRS
Copyright_xml – notice: 2008 Elsevier Ltd
– notice: 2009 INIST-CNRS
DBID 1KM
BLEPL
DTL
GDOUO
IQODW
AAYXX
CITATION
DOI 10.1016/j.tet.2008.11.025
DatabaseName Index Chemicus
Web of Science Core Collection
Science Citation Index Expanded
Web of Science - Science Citation Index Expanded - 2009
Pascal-Francis
CrossRef
DatabaseTitle Web of Science
CrossRef
DatabaseTitleList
Web of Science
Database_xml – sequence: 1
  dbid: 1KM
  name: Index Chemicus
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC
  sourceTypes:
    Enrichment Source
    Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1464-5416
EndPage 606
ExternalDocumentID 10_1016_j_tet_2008_11_025
21047576
000262773800002
S0040402008019637
GroupedDBID ---
--K
--M
-DZ
-ET
-~X
.GJ
.~1
0R~
123
186
1B1
1RT
1~.
1~5
29Q
4.4
457
4G.
53G
5RE
5VS
6TJ
7-5
71M
8P~
9JM
9JN
AABNK
AACTN
AAEDT
AAEDW
AAIAV
AAIKC
AAIKJ
AAKOC
AALRI
AAMNW
AAOAW
AAQFI
AAQXK
AARLI
AATCM
AAXUO
AAYJJ
ABEFU
ABFNM
ABGSF
ABJNI
ABMAC
ABPPZ
ABUDA
ABXDB
ABYKQ
ABZDS
ACBNA
ACDAQ
ACGFS
ACKIV
ACNCT
ACNNM
ACRLP
ADBBV
ADECG
ADEZE
ADMUD
ADUVX
AEBSH
AEHWI
AEKER
AENEX
AETEA
AFFNX
AFKWA
AFMIJ
AFTJW
AFXIZ
AFZHZ
AGHFR
AGRDE
AGUBO
AGYEJ
AHHHB
AIEXJ
AIKHN
AITUG
AJBFU
AJOXV
AJSZI
ALCLG
ALMA_UNASSIGNED_HOLDINGS
AMFUW
AMRAJ
ASPBG
AVWKF
AXJTR
AZFZN
BKOJK
BLXMC
CS3
DOVZS
DU5
EBS
EFJIC
EFLBG
EJD
EO8
EO9
EP2
EP3
F5P
FDB
FEDTE
FGOYB
FIRID
FLBIZ
FNPLU
FYGXN
G-Q
G8K
GBLVA
HMS
HVGLF
HZ~
IHE
J1W
K-O
KOM
M2Z
M41
MO0
MVM
N9A
NEJ
O-L
O9-
OAUVE
OGGZJ
OHT
OZT
P-8
P-9
P2P
PC.
PVJ
Q38
R2-
RIG
RNS
ROL
RPZ
SCB
SCC
SDF
SDG
SDP
SES
SEW
SOC
SPC
SPCBC
SSK
SSP
SSU
T5K
TN5
TWZ
UQL
WH7
WUQ
XFK
XOL
XPP
XSW
YK3
YR2
ZCG
ZKB
ZMT
~G-
1KM
AAHBH
AAXKI
ADVLN
AKRWK
BLEPL
DTL
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
AAPBV
ABPIF
ABPTK
IQODW
AAYXX
AFJKZ
CITATION
ID FETCH-LOGICAL-c327t-f379a72527c7174528b6e885e68aefb79f68ed5203feb2ebc10b28a7ae8966023
IEDL.DBID .~1
ISICitedReferencesCount 9
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000262773800002
ISSN 0040-4020
IngestDate Thu Sep 26 17:56:57 EDT 2024
Sun Oct 22 16:07:09 EDT 2023
Wed Sep 18 07:47:52 EDT 2024
Fri Oct 25 20:16:53 EDT 2024
Fri Feb 23 02:22:57 EST 2024
IsPeerReviewed true
IsScholarly true
Issue 3
Keywords 5-Thiosugar
Hetero-Diels–Alder reaction
Pummerer rearrangement
C-inside form
Optical resolution
Hetero-Diels-Alder reaction
Ab initio method
Pummerer reaction
Theoretical study
Oside
Thermodynamic stability
Organic sulfide
Thioaldehyde
Threo stereoisomer
Thioglycoside
Hetero Diels Alder reaction
Chemical synthesis
Language English
License CC BY 4.0
LinkModel DirectLink
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-c327t-f379a72527c7174528b6e885e68aefb79f68ed5203feb2ebc10b28a7ae8966023
PageCount 8
ParticipantIDs crossref_primary_10_1016_j_tet_2008_11_025
pascalfrancis_primary_21047576
webofscience_primary_000262773800002
webofscience_primary_000262773800002CitationCount
elsevier_sciencedirect_doi_10_1016_j_tet_2008_11_025
PublicationCentury 2000
PublicationDate 2009-01-17
PublicationDateYYYYMMDD 2009-01-17
PublicationDate_xml – month: 01
  year: 2009
  text: 2009-01-17
  day: 17
PublicationDecade 2000
PublicationPlace OXFORD
PublicationPlace_xml – name: OXFORD
– name: Kidlington
PublicationTitle Tetrahedron
PublicationTitleAbbrev TETRAHEDRON
PublicationYear 2009
Publisher Elsevier Ltd
Elsevier
Publisher_xml – name: Elsevier Ltd
– name: Elsevier
References Eliel, Wilen (bib16) 1994
Brunet, Eliel, Buchanan (bib21) 1986; 51
Yuasa, Tsuruta, Hashimoto, Baudry, Barberousse, Collette, Descotes, Pires, Samreth (bib22) 2007; 48
Yuasa, Jouyabu, Mitsuhashi, Hashimoto (bib7) 2008
Fujita, Matsuda, Yamamoto, Morii, Hashimoto, Okuno, Hashimoto (bib19) 2004; 60
Pummerer, Oae, Itoh, Numata, Yoshimura (bib18) 1910; 43
Hagameyer, Hull (bib11) 1949; 41
Carlson, Hill (bib8) 1988; 6
Haras, Culea, Masson, Phiouze, Vedejs, Eberlein, Mazur, McClure, Perry, Ruggeri, Schwartz, Stults, Varie, Wilde, Wittenberger, Adam, Freer, Isaacs, Kirby, Littlejohn, Rahman, Prabhakaran, Lhermitte, Das, Sasi-Kumar, Grierson (bib10) 2004; 51
Matsuda, Fujita, Morii, Hashimoto, Okuno, Hashimoto (bib12) 2003; 44
Vedejs, Rerry, Houk, Clark, Schleyer (bib13) 1983; 105
For example
Trost, Godleski, Ippen (bib9) 1978; 43
Sakakibara, T.; Nagano, C.; Hishinuma, K. Unpublished data.
Bozo, Boros, Kuszmann (bib2) 1998; 311
Capon, MacLeod (bib4) 1987
Korytnyk, Angelio, Dodson-Simmons, Hanchak, Madson, Valenteckovic-Horvath (bib1) 1983; 113
Witczak, Culhane (bib3) 2005; 69
Juaristi, Cuevas (bib6) 1992; 48
Buss, Hirst, Philip (bib15) 1987; 24
Frisch, Trucks, Schlegel, Scuseria, Robb, Cheeseman, Zakrzewski, Montgomery, Stratmann, Burant, Dapprich, Millam, Daniels, Kudin, Strain, Farkas, Tomasi, Barone, Cossi, Cammi, Mennucci, Pomelli, Adamo, Clifford, Ochterski, Petersson, Ayala, Cui, Morokuma, Malick, Rabuck, Raghavachari, Foresman, Cioslowski, Ortiz, Baboul, Stefanov, Liu, Liashenko, Piskorz, Komaromi, Gomperts, Martin, Fox, Keith, Al-Laham, Peng, Nanayakkara, Challacombe, Gill, Johnson, Chen, Wong, Andres, Gonzalez, Head-Gordon, Replogle, Pople (bib14) 1998
Jeong, Lee, Jacobsen, Kim, Shin, Lee, Gao, Lu, Doung, Gunaga, Lee, Jin, Chun, Moon (bib20) 2006; 49
VEDEJS, E (WOS:A1986C268000034) 1986; 51
BRUNET, E (WOS:A1986A394700018) 1986; 51
HAGAMEYER HJ (WOS:000262773800002.12) 1949; 41
ADAM, D (WOS:A1992HW16700012) 1992
Prabhakaran, J (WOS:000087091500025) 2000
TROST, BM (WOS:A1978FX60500001) 1978; 43
Baudry, M (WOS:000076524200006) 1998; 54
Witczak, ZJ (WOS:000234253600001) 2005; 69
BUSS DA (WOS:000262773800002.6) 1987; 24
FRISCH MJ (WOS:000262773800002.10) 1998
Jeong, LS (WOS:000234575300028) 2006; 49
Hughes, NA (WOS:000087764600007) 2000; 326
Matsuda, H (WOS:000182911500019) 2003; 44
SAKAKIBARA T (WOS:000262773800002.24)
HARAS M (WOS:000262773800002.13) 2004
YUASA H (WOS:000262773800002.30) 2008
OAE, S (WOS:A1983QA27400051) 1983; 56
CARLSON RM (WOS:000262773800002.8) 1988; 6
Pummerer, R (WOS:000201158400038) 1910; 43
MERRER YL (WOS:000262773800002.19) 1997; 49
KORYTNYK, W (WOS:A1983QF70700017) 1983; 113
NAYAK, UG (WOS:A1969C497200023) 1969; 34
Fujita, J (WOS:000222925500010) 2004; 60
CAPON, RJ (WOS:A1987J558200041) 1987
Yuasa, H (WOS:000252096900009) 2007; 48
BUCHANAN, GW (WOS:A1975AA76200008) 1975
JUARISTI, E (WOS:A1992JA14700001) 1992; 48
Bozó, E (WOS:000076876800003) 1998; 311
VEDEJS, E (WOS:A1983RQ99400061) 1983; 105
ELIEL EL (WOS:000262773800002.9) 1994
Buchanan (10.1016/j.tet.2008.11.025_bib21b) 1975; 25
Merrer (10.1016/j.tet.2008.11.025_bib5b) 1997; 49
Hughes (10.1016/j.tet.2008.11.025_bib5c) 2000; 326
Yuasa (10.1016/j.tet.2008.11.025_bib7) 2008
Korytnyk (10.1016/j.tet.2008.11.025_bib1) 1983; 113
Prabhakaran (10.1016/j.tet.2008.11.025_bib10d) 2000
Bozo (10.1016/j.tet.2008.11.025_bib2) 1998; 311
10.1016/j.tet.2008.11.025_bib17
Trost (10.1016/j.tet.2008.11.025_bib9) 1978; 43
Pummerer (10.1016/j.tet.2008.11.025_bib18a) 1910; 43
Capon (10.1016/j.tet.2008.11.025_bib4) 1987
Oae (10.1016/j.tet.2008.11.025_bib18b) 1983; 56
Matsuda (10.1016/j.tet.2008.11.025_bib12) 2003; 44
Vedejs (10.1016/j.tet.2008.11.025_bib10b) 1986; 51
Carlson (10.1016/j.tet.2008.11.025_bib8) 1988; 6
Eliel (10.1016/j.tet.2008.11.025_bib16) 1994
Baudry (10.1016/j.tet.2008.11.025_bib22b) 1998; 54
10.1016/j.tet.2008.11.025_bib5_1
Fujita (10.1016/j.tet.2008.11.025_bib19) 2004; 60
Frisch (10.1016/j.tet.2008.11.025_bib14) 1998
Yuasa (10.1016/j.tet.2008.11.025_bib22a) 2007; 48
Nayak (10.1016/j.tet.2008.11.025_bib5a) 1969; 34
Brunet (10.1016/j.tet.2008.11.025_bib21a) 1986; 51
Jeong (10.1016/j.tet.2008.11.025_bib20) 2006; 49
Hagameyer (10.1016/j.tet.2008.11.025_bib11) 1949; 41
Adam (10.1016/j.tet.2008.11.025_bib10c) 1992
Vedejs (10.1016/j.tet.2008.11.025_bib13) 1983; 105
Witczak (10.1016/j.tet.2008.11.025_bib3) 2005; 69
Buss (10.1016/j.tet.2008.11.025_bib15) 1987; 24
Juaristi (10.1016/j.tet.2008.11.025_bib6) 1992; 48
Haras (10.1016/j.tet.2008.11.025_bib10a) 2004
References_xml – year: 2008
  ident: bib7
  publication-title: Res. Lett. Org. Chem.
  contributor:
    fullname: Hashimoto
– volume: 48
  start-page: 7953
  year: 2007
  end-page: 7956
  ident: bib22
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Samreth
– year: 1994
  ident: bib16
  article-title: Stereochemistry of Organic Compounds
  contributor:
    fullname: Wilen
– volume: 69
  start-page: 237
  year: 2005
  end-page: 244
  ident: bib3
  publication-title: Appl. Microbiol. Biotechnol.
  contributor:
    fullname: Culhane
– volume: 44
  start-page: 4089
  year: 2003
  end-page: 4093
  ident: bib12
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Hashimoto
– volume: 60
  start-page: 6829
  year: 2004
  end-page: 6851
  ident: bib19
  publication-title: Tetrahedron
  contributor:
    fullname: Hashimoto
– start-page: 1200
  year: 1987
  end-page: 1201
  ident: bib4
  publication-title: J. Chem. Soc., Chem. Commun.
  contributor:
    fullname: MacLeod
– volume: 51
  start-page: 160
  year: 2004
  end-page: 172
  ident: bib10
  publication-title: Eur. J. Org. Chem.
  contributor:
    fullname: Grierson
– volume: 48
  start-page: 5019
  year: 1992
  end-page: 5087
  ident: bib6
  publication-title: Tetrahedron
  contributor:
    fullname: Cuevas
– volume: 41
  start-page: 2920
  year: 1949
  end-page: 2924
  ident: bib11
  publication-title: J. Ind. Eng. Chem.
  contributor:
    fullname: Hull
– volume: 311
  start-page: 191
  year: 1998
  end-page: 202
  ident: bib2
  publication-title: Carbohydr. Res.
  contributor:
    fullname: Kuszmann
– year: 1998
  ident: bib14
  article-title: GAUSSIAN 98, Revision A.9
  contributor:
    fullname: Pople
– volume: 43
  start-page: 1401
  year: 1910
  end-page: 1412
  ident: bib18
  publication-title: Chem. Ber.
  contributor:
    fullname: Yoshimura
– volume: 49
  start-page: 273
  year: 2006
  end-page: 281
  ident: bib20
  publication-title: J. Med. Chem.
  contributor:
    fullname: Moon
– volume: 24
  start-page: 1836
  year: 1987
  end-page: 1837
  ident: bib15
  publication-title: J. Chem. Soc. Chem. Commun.
  contributor:
    fullname: Philip
– volume: 113
  start-page: 166
  year: 1983
  end-page: 171
  ident: bib1
  publication-title: Carbohydr. Res.
  contributor:
    fullname: Valenteckovic-Horvath
– volume: 6
  start-page: 196
  year: 1988
  end-page: 198
  ident: bib8
  publication-title: Org. Synth. Collect. Vol.
  contributor:
    fullname: Hill
– volume: 43
  start-page: 4559
  year: 1978
  end-page: 4564
  ident: bib9
  publication-title: J. Org. Chem.
  contributor:
    fullname: Ippen
– volume: 51
  start-page: 677
  year: 1986
  end-page: 686
  ident: bib21
  publication-title: J. Org. Chem.
  contributor:
    fullname: Buchanan
– volume: 105
  start-page: 6999
  year: 1983
  end-page: 7001
  ident: bib13
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Schleyer
– volume: 69
  start-page: 237
  year: 2005
  ident: WOS:000234253600001
  article-title: Thiosugars: new perspectives regarding availability and potential biochemical and medicinal applications
  publication-title: APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
  doi: 10.1007/s00253-005-0156-x
  contributor:
    fullname: Witczak, ZJ
– volume: 48
  start-page: 5019
  year: 1992
  ident: WOS:A1992JA14700001
  article-title: RECENT STUDIES OF THE ANOMERIC EFFECT
  publication-title: TETRAHEDRON
  contributor:
    fullname: JUARISTI, E
– volume: 311
  start-page: 191
  year: 1998
  ident: WOS:000076876800003
  article-title: Synthesis of 4-cyanophenyl and 4-nitrophenyl 1,5-dithio-L- and -D-arabinopyranosides possessing antithrombotic activity
  publication-title: CARBOHYDRATE RESEARCH
  contributor:
    fullname: Bozó, E
– volume: 51
  start-page: 677
  year: 1986
  ident: WOS:A1986A394700018
  article-title: CONFORMATIONAL-ANALYSIS .46. CONFORMATIONAL EQUILIBRIA IN 3-HYDROXYTHIANES, 3-METHOXYTHIANES, AND 3-ACETOXYTHIANES, THEIR SULFOXIDES AND SULFONES, AND SOME CORRESPONDING 3-METHYL HOMOLOGS
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: BRUNET, E
– start-page: 658
  year: 2000
  ident: WOS:000087091500025
  article-title: The synthesis of a sulfone containing analogue of the esperamicin-A1 aglycone:: A hetero Diels-Alder approach
  publication-title: SYNLETT
  contributor:
    fullname: Prabhakaran, J
– start-page: 1261
  year: 1992
  ident: WOS:A1992HW16700012
  article-title: SYNTHESIS OF A THIASHIKIMIC ACID-DERIVATIVE
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
  contributor:
    fullname: ADAM, D
– volume: 105
  start-page: 6999
  year: 1983
  ident: WOS:A1983RQ99400061
  article-title: REGIOCHEMISTRY IN THIOCARBONYL DIELS-ALDER ADDITIONS - REVERSAL OF SELECTIVITY BY SUBSTITUENT EFFECTS IN THIOALDEHYDES
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: VEDEJS, E
– volume: 51
  start-page: 1556
  year: 1986
  ident: WOS:A1986C268000034
  article-title: THIOALDEHYDE DIELS-ALDER REACTIONS
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: VEDEJS, E
– volume: 56
  start-page: 270
  year: 1983
  ident: WOS:A1983QA27400051
  article-title: INTERMOLECULAR STEREOSELECTIVE PUMMERER REACTIONS OF 4-(PARA-CHLOROPHENYL)THIANE 1-OXIDES AND TRANS-1-THIADECALIN 1-OXIDES AND 2-THIADECALIN 2-OXIDES WITH ACETIC-ANHYDRIDE
  publication-title: BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
  contributor:
    fullname: OAE, S
– start-page: 696
  year: 1994
  ident: WOS:000262773800002.9
  publication-title: STEREOCHEMISTRY ORGA
  contributor:
    fullname: ELIEL EL
– volume: 49
  start-page: 273
  year: 2006
  ident: WOS:000234575300028
  article-title: Structure-activity relationships of 2-chloro-N6-substituted-4′-thioadenosine-5′-uronamides as highly potent and selective agonists at the human A3 adenosine receptor
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm050595e
  contributor:
    fullname: Jeong, LS
– start-page: 160
  year: 2004
  ident: WOS:000262773800002.13
  publication-title: EUR J ORG CHEM
  contributor:
    fullname: HARAS M
– volume: 34
  start-page: 97
  year: 1969
  ident: WOS:A1969C497200023
  article-title: IMPROVED SYNTHESES OF 5-THIO-D-GLUCOSE
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: NAYAK, UG
– ident: WOS:000262773800002.24
  publication-title: UNPUB
  contributor:
    fullname: SAKAKIBARA T
– volume: 43
  start-page: 4559
  year: 1978
  ident: WOS:A1978FX60500001
  article-title: STEREOCONTROLLED APPROACH TO 1,4-DISUBSTITUTED 1,3-DIENES
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: TROST, BM
– year: 1998
  ident: WOS:000262773800002.10
  publication-title: GAUSSIAN 98 REVISION
  contributor:
    fullname: FRISCH MJ
– volume: 60
  start-page: 6829
  year: 2004
  ident: WOS:000222925500010
  article-title: Synthesis of thiosaccharides employing the Pummerer rearrangement of tetrahydrothiopyran oxides
  publication-title: TETRAHEDRON
  doi: 10.1016/j.tet.2004.06.006
  contributor:
    fullname: Fujita, J
– start-page: 1200
  year: 1987
  ident: WOS:A1987J558200041
  article-title: 5-THIO-D-MANNOSE FROM THE MARINE SPONGE CLATHRIA-PYRAMIDA (LENDENFELD) - THE 1ST EXAMPLE OF A NATURALLY-OCCURRING 5-THIOSUGAR
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS
  contributor:
    fullname: CAPON, RJ
– volume: 43
  start-page: 1401
  year: 1910
  ident: WOS:000201158400038
  article-title: On phenyl sulfoxy-acetic acid. (II.)
  publication-title: BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT
  contributor:
    fullname: Pummerer, R
– volume: 113
  start-page: 166
  year: 1983
  ident: WOS:A1983QF70700017
  article-title: SYNTHESIS AND CONFORMATION OF 5-THIO-D-GLUCAL, AN INHIBITOR OF GLYCOSIDASES
  publication-title: CARBOHYDRATE RESEARCH
  contributor:
    fullname: KORYTNYK, W
– volume: 54
  start-page: 13783
  year: 1998
  ident: WOS:000076524200006
  article-title: Synthetic studies in the 5-thio-D-xylopyranose series -: part 3:: Preparations of O-phenyl and C-(4-hydroxyphenyl) 5-thio-D-xylopyranosides
  publication-title: TETRAHEDRON
  contributor:
    fullname: Baudry, M
– start-page: 1683
  year: 1975
  ident: WOS:A1975AA76200008
  article-title: NEW APPROACH TO DETERMINATION OF SULFOXIDE STEREOCHEMISTRY - C-13 NUCLEAR MAGNETIC-RESONANCE
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: BUCHANAN, GW
– year: 2008
  ident: WOS:000262773800002.30
  publication-title: RES LETT ORG CHEM
  contributor:
    fullname: YUASA H
– volume: 41
  start-page: 2920
  year: 1949
  ident: WOS:000262773800002.12
  publication-title: J IND ENG CHEM
  contributor:
    fullname: HAGAMEYER HJ
– volume: 24
  start-page: 1836
  year: 1987
  ident: WOS:000262773800002.6
  publication-title: J CHEM SOC CHEM COMM
  contributor:
    fullname: BUSS DA
– volume: 44
  start-page: 4089
  year: 2003
  ident: WOS:000182911500019
  article-title: Pummerer rearrangement of 1-deoxy-5-thioglucopyranose oxides; novel synthesis of 5-thioglucopyranose derivatives
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/S0040-4039(03)00842-6
  contributor:
    fullname: Matsuda, H
– volume: 48
  start-page: 7953
  year: 2007
  ident: WOS:000252096900009
  article-title: A novel 5-thioglycosylation method with 1,5-dithioglycosyl donors: relevance to exo- versus endocyclic activation
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2007.09.056
  contributor:
    fullname: Yuasa, H
– volume: 49
  start-page: 16731
  year: 1997
  ident: WOS:000262773800002.19
  publication-title: TETRAHEDRON LETT
  contributor:
    fullname: MERRER YL
– volume: 6
  start-page: 196
  year: 1988
  ident: WOS:000262773800002.8
  publication-title: ORG SYNTH
  contributor:
    fullname: CARLSON RM
– volume: 326
  start-page: 323
  year: 2000
  ident: WOS:000087764600007
  article-title: Synthesis of 5-thio-L-altrose
  publication-title: CARBOHYDRATE RESEARCH
  contributor:
    fullname: Hughes, NA
– year: 2008
  ident: 10.1016/j.tet.2008.11.025_bib7
  publication-title: Res. Lett. Org. Chem.
  contributor:
    fullname: Yuasa
– volume: 60
  start-page: 6829
  year: 2004
  ident: 10.1016/j.tet.2008.11.025_bib19
  publication-title: Tetrahedron
  doi: 10.1016/j.tet.2004.06.006
  contributor:
    fullname: Fujita
– volume: 311
  start-page: 191
  year: 1998
  ident: 10.1016/j.tet.2008.11.025_bib2
  publication-title: Carbohydr. Res.
  doi: 10.1016/S0008-6215(98)00221-3
  contributor:
    fullname: Bozo
– volume: 44
  start-page: 4089
  year: 2003
  ident: 10.1016/j.tet.2008.11.025_bib12
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(03)00842-6
  contributor:
    fullname: Matsuda
– volume: 105
  start-page: 6999
  year: 1983
  ident: 10.1016/j.tet.2008.11.025_bib13
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja00361a062
  contributor:
    fullname: Vedejs
– start-page: 1261
  year: 1992
  ident: 10.1016/j.tet.2008.11.025_bib10c
  publication-title: J. Chem. Soc., Perkin Trans. 1
  doi: 10.1039/p19920001261
  contributor:
    fullname: Adam
– volume: 41
  start-page: 2920
  year: 1949
  ident: 10.1016/j.tet.2008.11.025_bib11
  publication-title: J. Ind. Eng. Chem.
  doi: 10.1021/ie50480a063
  contributor:
    fullname: Hagameyer
– start-page: 658
  year: 2000
  ident: 10.1016/j.tet.2008.11.025_bib10d
  publication-title: Synlett
  contributor:
    fullname: Prabhakaran
– volume: 48
  start-page: 5019
  year: 1992
  ident: 10.1016/j.tet.2008.11.025_bib6
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(01)90118-8
  contributor:
    fullname: Juaristi
– volume: 25
  start-page: 1683
  year: 1975
  ident: 10.1016/j.tet.2008.11.025_bib21b
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)72232-5
  contributor:
    fullname: Buchanan
– year: 1994
  ident: 10.1016/j.tet.2008.11.025_bib16
  contributor:
    fullname: Eliel
– volume: 56
  start-page: 270
  year: 1983
  ident: 10.1016/j.tet.2008.11.025_bib18b
  publication-title: Bull. Chem. Soc. Jpn.
  doi: 10.1246/bcsj.56.270
  contributor:
    fullname: Oae
– volume: 54
  start-page: 13783
  year: 1998
  ident: 10.1016/j.tet.2008.11.025_bib22b
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(98)00848-5
  contributor:
    fullname: Baudry
– volume: 69
  start-page: 237
  year: 2005
  ident: 10.1016/j.tet.2008.11.025_bib3
  publication-title: Appl. Microbiol. Biotechnol.
  doi: 10.1007/s00253-005-0156-x
  contributor:
    fullname: Witczak
– volume: 48
  start-page: 7953
  year: 2007
  ident: 10.1016/j.tet.2008.11.025_bib22a
  publication-title: Tetrahedron Lett.
  doi: 10.1016/j.tetlet.2007.09.056
  contributor:
    fullname: Yuasa
– volume: 49
  start-page: 273
  year: 2006
  ident: 10.1016/j.tet.2008.11.025_bib20
  publication-title: J. Med. Chem.
  doi: 10.1021/jm050595e
  contributor:
    fullname: Jeong
– start-page: 1200
  year: 1987
  ident: 10.1016/j.tet.2008.11.025_bib4
  publication-title: J. Chem. Soc., Chem. Commun.
  doi: 10.1039/c39870001200
  contributor:
    fullname: Capon
– start-page: 160
  year: 2004
  ident: 10.1016/j.tet.2008.11.025_bib10a
  publication-title: Eur. J. Org. Chem.
  doi: 10.1002/ejoc.200300334
  contributor:
    fullname: Haras
– volume: 43
  start-page: 4559
  year: 1978
  ident: 10.1016/j.tet.2008.11.025_bib9
  publication-title: J. Org. Chem.
  doi: 10.1021/jo00418a001
  contributor:
    fullname: Trost
– volume: 24
  start-page: 1836
  year: 1987
  ident: 10.1016/j.tet.2008.11.025_bib15
  publication-title: J. Chem. Soc. Chem. Commun.
  doi: 10.1039/C39870001836
  contributor:
    fullname: Buss
– volume: 51
  start-page: 1556
  year: 1986
  ident: 10.1016/j.tet.2008.11.025_bib10b
  publication-title: J. Org. Chem.
  doi: 10.1021/jo00359a034
  contributor:
    fullname: Vedejs
– volume: 34
  start-page: 97
  year: 1969
  ident: 10.1016/j.tet.2008.11.025_bib5a
  publication-title: J. Org. Chem.
  doi: 10.1021/jo00838a023
  contributor:
    fullname: Nayak
– ident: 10.1016/j.tet.2008.11.025_bib5_1
– volume: 43
  start-page: 1401
  year: 1910
  ident: 10.1016/j.tet.2008.11.025_bib18a
  publication-title: Chem. Ber.
  doi: 10.1002/cber.19100430241
  contributor:
    fullname: Pummerer
– volume: 326
  start-page: 323
  year: 2000
  ident: 10.1016/j.tet.2008.11.025_bib5c
  publication-title: Carbohydr. Res.
  doi: 10.1016/S0008-6215(00)00052-5
  contributor:
    fullname: Hughes
– volume: 51
  start-page: 677
  year: 1986
  ident: 10.1016/j.tet.2008.11.025_bib21a
  publication-title: J. Org. Chem.
  doi: 10.1021/jo00355a018
  contributor:
    fullname: Brunet
– volume: 49
  start-page: 16731
  year: 1997
  ident: 10.1016/j.tet.2008.11.025_bib5b
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(97)10096-5
  contributor:
    fullname: Merrer
– ident: 10.1016/j.tet.2008.11.025_bib17
– volume: 113
  start-page: 166
  year: 1983
  ident: 10.1016/j.tet.2008.11.025_bib1
  publication-title: Carbohydr. Res.
  doi: 10.1016/0008-6215(83)88230-5
  contributor:
    fullname: Korytnyk
– year: 1998
  ident: 10.1016/j.tet.2008.11.025_bib14
  contributor:
    fullname: Frisch
– volume: 6
  start-page: 196
  year: 1988
  ident: 10.1016/j.tet.2008.11.025_bib8
  publication-title: Org. Synth. Collect. Vol.
  contributor:
    fullname: Carlson
SSID ssj0001123
Score 2.0152354
Snippet The title compound was prepared via hetero-Diels–Alder reaction of 1-acetoxy-1,3-butadiene and thioaldehyde, followed by Pummerer rearrangement. Different from...
The title compound was prepared via hetero-Diels-Alder reaction of 1-acetoxy-1,3-butadiene and thioaldehyde, followed by Pummerer rearrangement. Different from...
Source Web of Science
SourceID crossref
pascalfrancis
webofscience
elsevier
SourceType Aggregation Database
Index Database
Enrichment Source
Publisher
StartPage 599
SubjectTerms 5-Thiosugar
C-inside form
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Chemistry, Organic
Exact sciences and technology
Hetero-Diels–Alder reaction
Optical resolution
Organic chemistry
Physical Sciences
Preparations and properties
Pummerer rearrangement
Science & Technology
Title Synthesis of methyl 4,6- O-benzylidene-2,3-dideoxy-5-thio-β- dl- threo-hex-2-enopyranoside via hetero-Diels–Alder reaction and unusual stabilities of 1,5-anhydro-4,6- O-benzylidene 2,3-dideoxy-5-thio- dl- threo-hex-2-enitol
URI https://dx.doi.org/10.1016/j.tet.2008.11.025
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000262773800002
Volume 65
WOS 000262773800002
WOSCitedRecordID wos000262773800002
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3NitRAEG6W9aAg4i-Oq0Mf9iRTbrqTTifHYXQZFdeDLuwtJJ1uJsuQDE5GNnsQ38E38UF8iH0Sq_IzujiIeAtJh1RSlaqv6Kr6GDvUQuTaZDmksVEQaDyKPReDEcqgo_SMVtTv_O4knJ8Gb87U2R6bDb0wVFbZ-_7Op7feuj9z1H_No1VRUI9v4FH2g5iHzIg6ymnYFtr0iy-_yjwQT2wr52j1sLPZ1njVti-npEGexJa9OzbdXqVr_GKuo7rYGaLacHR8l93pcSSfdqLeY3u2vM9uzgb6tgfs6kNTIrhbF2teOU5E0c2SB5MQ-HvIbHnZLIlO1IKc-JDjYXXRgIJ6UVTw4zvwfAm8Rj1XsLAXIMGW1apBySqi9-Sfi5QvqJCmgpcFvsHV129TovvmCEHbRgmeljnflJv1BoVEANqW4GJSTrKIiYK0XDQ53v2nQHyHQDukQUe0fMhOj199nM2hJ3QA40tdg_N1nGqppDaYRQZKRlloo0jZMEqty3TswsjmSnq-w4TfZkZ4mYxSndqIhohK_xHbL6vSPmY8jGMXZYEQJg8CF7kYV5tcWOVihKBGjdjzQZXJqpvbkQwFbecJ6r3j38TsB_U-YsGg7OSa8SUYV_522_iaYWwfJGn-BSZyI3b4u6Vsr1MYCqXWfkRwQY6Y-Jdls35oOw0rqJ_8n8gH7Fa3HSZA6Kdsv_60sc8QVdXZuP1txuzG9PXb-clPBVUiow
link.rule.ids 315,783,787,4511,24130,27938,27939,45599,45693
linkProvider Elsevier
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3NbtQwELZKeygSQvyK5af40BPaUddOHNvH1UK1pe1yoJV6ixLH1gatkhWbRQ0n3oE34UF4iD4J4_ysqFghxC1KbGXimcx8I4_nI-RQMpZJk2aQaCMglHilR06DYcKgoxwZKfx55_NZNL0M31-Jqx0y6c_C-LLKzve3Pr3x1t2do241j5Z57s_4hiOf_SDm8WYk75A9RAMajX1vfHI6nW0cMkKKTfGcn9BvbjZlXpXtKip9L09PmL09PN1bJitcNNeyXWyNUk1EOn5A7ndQko5baR-SHVs8IvuTnsHtMbn5WBeI71b5ipaOeq7oekHDYQT0A6S2-FovPKOoBT4MIMPL8roGAdU8L-HnD6DZAmiFqi5hbq-Bgy3KZY2SlZ7hk37JEzr3tTQlvM3xC26-fR97xm-KKLQ5K0GTIqPrYr1ao5CIQZsqXMzLvSxsKCAp5nWGs_8UiG4RaIs06IsWT8jl8buLyRQ6TgcwAZcVuEDqRHLBpcFEMhRcpZFVSthIJdalUrtI2UzwUeAw57epYaOUq0QmVvk-ojx4SnaLsrDPCI20dioNGTNZGDrlNI42GbPCaUShRgzIm16V8bJt3RH3NW2fYtR7S8GJCRDqfUDCXtnxLfuLMbT8bdrBLcPYvIj7FhiYyw3I4e-WsnnuI1HEpQyURwx8QNi_DJt0fdt9v4Lq-f-J_JrsTy_Oz-Kzk9npC3K33R1jwORLslt9XttXCLKq9KD7iX4BCoIlYA
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Synthesis+of+methyl+4%2C6-+O-benzylidene-2%2C3-dideoxy-5-thio-%CE%B2-+dl-+threo-hex-2-enopyranoside+via+hetero-Diels%E2%80%93Alder+reaction+and+unusual+stabilities+of+1%2C5-anhydro-4%2C6-+O-benzylidene+2%2C3-dideoxy-5-thio-+dl-+threo-hex-2-enitol&rft.jtitle=Tetrahedron&rft.au=Watanabe%2C+Yuhya&rft.au=Sakakibara%2C+Tohru&rft.date=2009-01-17&rft.pub=Elsevier+Ltd&rft.issn=0040-4020&rft.eissn=1464-5416&rft.volume=65&rft.issue=3&rft.spage=599&rft.epage=606&rft_id=info:doi/10.1016%2Fj.tet.2008.11.025&rft.externalDocID=S0040402008019637
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0040-4020&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0040-4020&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0040-4020&client=summon