SYNTHESIS OF 2',3'-DIDEHYDRO-2',3'-DIDEOXYNUCLEOSIDES UTILIZING COUPLING REACTIONS BETWEEN NUCLEIC BASES AND PHENYLTHIO-SUBSTITUTED 2,3-DIDEOXYRIBOSE

被引：20

作者：

KAWAKAMI, H ^{[1
]}

EBATA, T ^{[1
]}

KOSEKI, K ^{[1
]}

MATSUMOTO, K ^{[1
]}

MATSUSHITA, H ^{[1
]}

NAOI, Y ^{[1
]}

ITOH, K ^{[1
]}

机构：

[1] YUKI GOSEI KOGYO LTD,TOKYO RES LAB,ITABASHI KU,TOKYO 174,JAPAN

来源：

HETEROCYCLES | 1991年 / 32卷 / 12期

关键词：

D O I：

10.3987/COM-91-5884

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselectivities in coupling reactions between silylated pyrimidine bases and 3- or 2-alpha-phenylthio-2,3-dideoxyribose were examined. In the former case, no stereoselectivies were observed when the coupling reactions were performed either with 1-chlorosugar in an S(N)2 mode or in the presence of Lewis acids as catalyst in an S(N)1 mode. Coupling reaction with 2-alpha-phenylthio-2,3-dideoxyribose in the presence of Lewis acids, especially SnCl4, proceeded with good stereoselectivity to give anomeric mixtures of alpha:beta = 1:9. All these nucleosides were converted to 2',3'-didehydro-2',3'-dideoxynucleosides by oxidation to sulfoxides followed by thermal elimination of sulfenic acid.

引用

页码：2451 / 2470

页数：20

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