Synthesis of 9-halogenated 9-deazaguanine N-7-(2 '-deoxyribonucleosides)
The syntheses of N-7-glycosylated 9-deazaguanine 1a as well as of its 9-bromo and 9-iodo derivatives 1b,c are described. The regioselective 9-halogenation with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) was accomplished at the protected nucleobase 4a (2-{[(dimethylamino)methylidene]amino}-...
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| Published in | Helvetica chimica acta Vol. 87; no. 10; pp. 2507 - 2516 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
01.10.2004
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| Abstract | The syntheses of N-7-glycosylated 9-deazaguanine 1a as well as of its 9-bromo and 9-iodo derivatives 1b,c are described. The regioselective 9-halogenation with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) was accomplished at the protected nucleobase 4a (2-{[(dimethylamino)methylidene]amino}-3,5-dihydro-3-[(pivaloyloxy)methyl]-4H-pyrrolo[3,2-d]pyrimidin-4-one). Nucleobase-anion glycosylation of 4a-c with 2-deoxy-3,5-di-O-(p-toluoyl)-alpha-D-erythro-pentofuranosyl chloride (5) furnished the fully protected intermediates 6a-c (Scheme 2). They were deprotected with 0.01M NaOMe yielding the sugar-deprotected derivatives 8a-c (Scheme 3). At higher concentrations (0.1M NaOMe), also the pivaloyloxymethyl group was removed to give 7a-c, while conc. aq. NH3 solution furnished the nucleosides 1a-c. In D2O, the sugar conformation was always biased towards S (67-61%). |
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| AbstractList | Abstract
The syntheses of
N
7
‐glycosylated 9‐deazaguanine
1a
as well as of its 9‐bromo and 9‐iodo derivatives
1b
,
c
are described. The regioselective 9‐halogenation with
N
‐bromosuccinimide (NBS) and
N
‐iodosuccinimide (NIS) was accomplished at the protected nucleobase
4a
(2‐{[(dimethylamino)methylidene]amino}‐3,5‐dihydro‐3‐[(pivaloyloxy)methyl]‐4
H
‐pyrrolo[3,2‐
d
]pyrimidin‐4‐one). Nucleobase‐anion glycosylation of
4a
–
c
with 2‐deoxy‐3,5‐di‐
O
‐(
p
‐toluoyl)‐α‐
D
‐
erythro
‐pentofuranosyl chloride (
5
) furnished the fully protected intermediates
6a
–
c
(
Scheme 2
). They were deprotected with 0.01
M
NaOMe yielding the sugar‐deprotected derivatives
8a
–
c
(
Scheme 3
). At higher concentrations (0.1
M
NaOMe), also the pivaloyloxymethyl group was removed to give
7a
–
c
, while conc. aq. NH
3
solution furnished the nucleosides
1a
–
c
. In D
2
O, the sugar conformation was always biased towards
S
(67–61%). The syntheses of N-7-glycosylated 9-deazaguanine 1a as well as of its 9-bromo and 9-iodo derivatives 1b,c are described. The regioselective 9-halogenation with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) was accomplished at the protected nucleobase 4a (2-{[(dimethylamino)methylidene]amino}-3,5-dihydro-3-[(pivaloyloxy)methyl]-4H-pyrrolo[3,2-d]pyrimidin-4-one). Nucleobase-anion glycosylation of 4a-c with 2-deoxy-3,5-di-O-(p-toluoyl)-alpha-D-erythro-pentofuranosyl chloride (5) furnished the fully protected intermediates 6a-c (Scheme 2). They were deprotected with 0.01M NaOMe yielding the sugar-deprotected derivatives 8a-c (Scheme 3). At higher concentrations (0.1M NaOMe), also the pivaloyloxymethyl group was removed to give 7a-c, while conc. aq. NH3 solution furnished the nucleosides 1a-c. In D2O, the sugar conformation was always biased towards S (67-61%). |
| Author | Wiglenda, T Seela, F Shaikh, KI Leonard, P |
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| CitedBy_id | crossref_primary_10_1002_cbic_201000162 crossref_primary_10_1002_hlca_200690063 crossref_primary_10_1039_b610930f crossref_primary_10_1002_chin_200509204 |
| Cites_doi | 10.1021/jo034048h 10.1093/nar/24.11.1987 10.1039/a808769e 10.1021/jo00129a040 10.1002/(SICI)1521-3765(19980904)4:9<1781::AID-CHEM1781>3.0.CO;2-K 10.1081/NCN-100002536 10.1021/jo00309a024 10.1002/hlca.19960790215 10.1002/hlca.19940770403 10.1080/00397919708007071 10.1002/hlca.19970800605 10.1016/0040-4020(80)80155-4 10.1080/07328319708002958 10.1093/nar/11.4.1167 10.1021/jm00053a008 10.1002/jhet.5570270302 10.1021/ja00114a036 10.1002/hlca.19950780505 10.1021/jm00065a007 10.1002/(SICI)1522-2675(19991006)82:10<1640::AID-HLCA1640>3.0.CO;2-N 10.1002/jhet.5570240354 10.1002/hlca.19960790605 10.1080/07328319808003464 10.1073/pnas.88.24.11540 10.1002/cber.19600931204 10.1002/hlca.19950780110 10.1021/ja00531a007 10.1021/jo990903e 10.1080/07328319708006203 |
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| Keywords | OLIGONUCLEOTIDE DUPLEXES SUGAR CONFORMATION PURINE NUCLEOSIDE PHOSPHORYLASE DNA STABILITY SUBSTITUENTS TRIPLE-HELIX FORMATION INHIBITORS DERIVATIVES STRUCTURE-BASED DESIGN |
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| Snippet | The syntheses of N-7-glycosylated 9-deazaguanine 1a as well as of its 9-bromo and 9-iodo derivatives 1b,c are described. The regioselective 9-halogenation with... Abstract The syntheses of N 7 ‐glycosylated 9‐deazaguanine 1a as well as of its 9‐bromo and 9‐iodo derivatives 1b , c are described. The regioselective... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology |
| Title | Synthesis of 9-halogenated 9-deazaguanine N-7-(2 '-deoxyribonucleosides) |
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