STEREOSPECIFIC SYNTHESIS OF OPTICALLY-ACTIVE 2-PHENYLSULFONYL-3-(1-HYDROXYETHYL)-4-AZETIDINONE - A PRECURSOR OF THIENAMYCIN-TYPE CARBAPENEMS

Stereospecific synthesis of optically active (2R,3S)-2-phenylsulfonyl-3-(1R-hydroxyethyl)-4-azetidinone from L-threonine is described. This compound is one of the key compounds for the synthesis of the thienamycin-type carbapenems.

Saved in:
Bibliographic Details
Published inHeterocycles Vol. 24; no. 4; pp. 1007 - 1012
Main Authors SHIOZAKI, M, HIRAOKA, T, YANAGISAWA, H, MARUYAMA, H, KISHI, N, ODA, O
Format Journal Article
LanguageEnglish
Published Tokyo Japan Inst Heterocyclic Chemistry 01.04.1986
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Online AccessGet more information

Cover

Abstract Stereospecific synthesis of optically active (2R,3S)-2-phenylsulfonyl-3-(1R-hydroxyethyl)-4-azetidinone from L-threonine is described. This compound is one of the key compounds for the synthesis of the thienamycin-type carbapenems.
AbstractList Stereospecific synthesis of optically active (2R,3S)-2-phenylsulfonyl-3-(1R-hydroxyethyl)-4-azetidinone from L-threonine is described. This compound is one of the key compounds for the synthesis of the thienamycin-type carbapenems.
Author YANAGISAWA, H
ODA, O
SHIOZAKI, M
HIRAOKA, T
KISHI, N
MARUYAMA, H
Author_xml – sequence: 1
  givenname: M
  surname: SHIOZAKI
  fullname: SHIOZAKI, M
– sequence: 2
  givenname: T
  surname: HIRAOKA
  fullname: HIRAOKA, T
– sequence: 3
  givenname: H
  surname: YANAGISAWA
  fullname: YANAGISAWA, H
– sequence: 4
  givenname: H
  surname: MARUYAMA
  fullname: MARUYAMA, H
– sequence: 5
  givenname: N
  surname: KISHI
  fullname: KISHI, N
– sequence: 6
  givenname: O
  surname: ODA
  fullname: ODA, O
BookMark eNqNkEFPgzAYhhszE7fp1TNHjfm0hULbY-06acKAQGfEywIMEowys2GM_8EfLYv-AE_P5cmTN-8MTfpd3yB0SfCtJzi7y4AIHgCmQDBmJ2hKOCeABXUnaIo97oNPCT1Ds8PhBWPMMedT9J1bnekkT7UyS6OcvIhtqHOTO8nSSVJrlIyiAqSy5lE7LqShjosoX0fLZCR4cEUgLBZZ8lRoGxbRNVCQz9qahYmTWDvgSCfNtFpneZIdmzY0OparQpkYbJFqR8nsXqY61qv8HJ225euhufjjHK2X2qoQouThOARqj7kDUFaP2xnloiwD3lR1TYOKMsZE07o-I5SJQPhbvyop53R0qL9tK6_aCo-wkgh3jm5-u59NtWsPddf0dbN533dv5f5rI483ygD7dHzJ5aPN_2-rbiiHbter3Uc_uD9hLW_m
CitedBy_id crossref_primary_10_1002_jhet_5570250225
crossref_primary_10_1246_bcsj_60_645
crossref_primary_10_1021_cr050528s
crossref_primary_10_1002_cmdc_201100282
crossref_primary_10_1002_chin_198643140
ContentType Journal Article
DBID 1KN
AAGGN
BLEPL
DTL
DOI 10.3987/R-1986-04-1007
DatabaseName Current Chemical Reactions
Web of Science - Science Citation Index Expanded - 1986
Web of Science Core Collection
Science Citation Index Expanded
DatabaseTitle Web of Science
DatabaseTitleList Web of Science
Database_xml – sequence: 1
  dbid: 1KN
  name: Current Chemical Reactions
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR
  sourceTypes:
    Enrichment Source
    Index Database
DeliveryMethod no_fulltext_linktorsrc
Discipline Chemistry
EISSN 1881-0942
EndPage 1012
ExternalDocumentID A1986A605400028
GroupedDBID -~X
1KN
3L6
53G
5GY
AENEX
AHWXS
AI.
ALMA_UNASSIGNED_HOLDINGS
B.R
BLEPL
CS3
DTL
DU5
EBS
EJD
F5P
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
P2P
SJN
TN5
UPT
VH1
Y6R
ZE2
ID FETCH-LOGICAL-c372t-47c0887489aa68ebcc46b47779ef2571479695d5ba4884aa645dfb3bd9317a192
ISICitedReferencesCount 7
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=A1986A605400028
ISSN 0385-5414
IngestDate Fri Jul 26 10:24:03 EDT 2024
Fri Oct 25 20:22:44 EDT 2024
IsDoiOpenAccess false
IsOpenAccess true
IsPeerReviewed true
IsScholarly true
Issue 4
Language English
LinkModel OpenURL
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-c372t-47c0887489aa68ebcc46b47779ef2571479695d5ba4884aa645dfb3bd9317a192
OpenAccessLink https://doi.org/10.3987/r-1986-04-1007
PageCount 6
ParticipantIDs webofscience_primary_A1986A605400028
webofscience_primary_A1986A605400028CitationCount
PublicationCentury 1900
PublicationDate 1986-04-01
PublicationDateYYYYMMDD 1986-04-01
PublicationDate_xml – month: 04
  year: 1986
  text: 1986-04-01
  day: 01
PublicationDecade 1980
PublicationPlace Tokyo
PublicationPlace_xml – name: Tokyo
PublicationTitle Heterocycles
PublicationTitleAbbrev HETEROCYCLES
PublicationYear 1986
Publisher Japan Inst Heterocyclic Chemistry
Publisher_xml – name: Japan Inst Heterocyclic Chemistry
References MARUYAMA, H (WOS:A1985ARC6300028) 1985; 26
LEANZA, WJ (WOS:A1983RH26500009) 1983; 39
KOBAYASHI, T (WOS:A1980KE51800041) 1980
NISHIDA, A (WOS:A1981MP85700017) 1981; 22
SHIOZAKI, M (WOS:A1981MT85100029) 1981; 22
YANAGISAWA, H (WOS:A1983QD75900017) 1983; 24
References_xml – volume: 24
  start-page: 1037
  year: 1983
  ident: WOS:A1983QD75900017
  article-title: SYNTHESIS OF OPTICALLY-ACTIVE AZETIDIN-2-ONES FROM L-THREONINE
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: YANAGISAWA, H
– volume: 22
  start-page: 5205
  year: 1981
  ident: WOS:A1981MT85100029
  article-title: STEREOCONTROLLED SYNTHESES OF CHIRAL INTERMEDIATES OF THIENAMYCIN FROM THREONINES
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: SHIOZAKI, M
– volume: 22
  start-page: 4819
  year: 1981
  ident: WOS:A1981MP85700017
  article-title: REGIOSELECTIVE TRANSFORMATION OF INTERNAL ALKYNES TO UNSYMMETRICAL KETONES - NOVEL ROUTES TO KEY INTERMEDIATES FOR THE SYNTHESIS OF CARBAPENEM AND CARBACEPHEM SKELETONS
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: NISHIDA, A
– start-page: 736
  year: 1980
  ident: WOS:A1980KE51800041
  article-title: A NEW METHOD FOR THE CARBON-EXTENSION REACTIONS OF AZETIDIN-2-ONES AT THE 4-POSITION
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS
  contributor:
    fullname: KOBAYASHI, T
– volume: 26
  start-page: 4521
  year: 1985
  ident: WOS:A1985ARC6300028
  article-title: CYCLIZATION REACTION OF N-PROPARGYL EPOXYAMIDE TO ACETYLENIC 2-AZETIDINONE, A PRECURSOR TO THIENAMYCIN AND RELATED CARBAPENEMS
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: MARUYAMA, H
– volume: 39
  start-page: 2505
  year: 1983
  ident: WOS:A1983RH26500009
  article-title: AN EFFICIENT SYNTHESIS OF 2-SUBSTITUTED-THIO-6-HYDROXYETHYL-PENEM-3-CARBOXYLIC ACIDS VIA 2-THIOXOPENAMS
  publication-title: TETRAHEDRON
  contributor:
    fullname: LEANZA, WJ
SSID ssj0008088
ssib055720442
Score 1.3263171
Snippet Stereospecific synthesis of optically active (2R,3S)-2-phenylsulfonyl-3-(1R-hydroxyethyl)-4-azetidinone from L-threonine is described. This compound is one of...
Source Web of Science
SourceID webofscience
SourceType Enrichment Source
Index Database
StartPage 1007
SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title STEREOSPECIFIC SYNTHESIS OF OPTICALLY-ACTIVE 2-PHENYLSULFONYL-3-(1-HYDROXYETHYL)-4-AZETIDINONE - A PRECURSOR OF THIENAMYCIN-TYPE CARBAPENEMS
URI http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=A1986A605400028
Volume 24
WOS A1986A605400028
WOSCitedRecordID wosA1986A605400028
hasFullText
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Lj9MwELa6cIAL4imWBZTDIoEqwzZxXkeTdZXQblIlKTR7WcVOInHpcuge4Dfwz_hTzCRpmlQ9FC5pZCWW6_k6D3fmG0LOdWSRcguHOqbuQoByIanDKh3uDOSCLnNZ1myfoeUv2ZeVuRqN_vSylu428qP6dbCu5H-kCmMgV6yS_QfJdpPCANyDfOEKEobrUTJOwBcVUbIQXjCF3UyyMPVFEtTtyKNFilQH84xinshXMdbpwhdhNk-W82kEn9SgSNJE_ewyjlaZSP1s_g53kvJrkQaXQRiFYkxBc4CUvGWcRHGTIhSIkF9lXhDSNFuIscfjz3whQtEeb7eero95NrfqJ2bddcc4fhBd81kwPIUNYh7N-CBhO8M-A0HCv_FB_cQVj5cZ_ifQDRZNAZ9j9dJcalsCPsC6zoQY7xbyXY29bX-7ngI0HJNim_LGVjUK2oGNgZB0oMGbKuwWqaynjjEFpGfakcvskNkw6oOXaUy369291-fn3rObXTYjx9e4hc4vhrAn5MR2al99Fm5Vm2liMyC2YzZzLuqWqN1XbPhEcSGfhss46BDVzk_6mDxqoxaNNxB8Qkbl-il50G3mM_J7CEWtg6IWTbV9KGoHoPh-CMQPQxhqVONaB0Occx-GWg-Gz8lyKlLPp22jD6oMW99QZis0dsxx89xySqkUsySzbdstKzApE2a7lmsWpszB3DB4hplFJQ1ZuOD95hCjvCD31rfr8iXRJrqubFWpfFKYTFa5q5dWyZRkqgLb5uan5Ly_nTc_Gk6Xmz0ZnpLJMY95LY8-8kdsXh039Rl5uPtZvCb3K1BG5RvwbDfybY2Zv8plhwo
link.rule.ids 783
linkProvider Clarivate
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=STEREOSPECIFIC+SYNTHESIS+OF+OPTICALLY-ACTIVE+2-PHENYLSULFONYL-3-%281-HYDROXYETHYL%29-4-AZETIDINONE+-+A+PRECURSOR+OF+THIENAMYCIN-TYPE+CARBAPENEMS&rft.jtitle=Heterocycles&rft.au=SHIOZAKI%2C+M&rft.au=HIRAOKA%2C+T&rft.au=YANAGISAWA%2C+H&rft.au=MARUYAMA%2C+H&rft.date=1986-04-01&rft.pub=Japan+Inst+Heterocyclic+Chemistry&rft.issn=0385-5414&rft.eissn=1881-0942&rft.volume=24&rft.issue=4&rft.spage=1007&rft.epage=1012&rft_id=info:doi/10.3987%2FR-1986-04-1007&rft.externalDBID=n%2Fa&rft.externalDocID=A1986A605400028
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0385-5414&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0385-5414&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0385-5414&client=summon