SYNTHESIS OF 2',3'-DIDEOXY-3'-C-HYDROXYMETHYL NUCLEOSIDES AS POTENTIAL INHIBITORS OF HIV

被引：91

作者：

SVANSSON, L

KVARNSTROM, I

CLASSON, B

SAMUELSSON, B

机构：

[1] UNIV STOCKHOLM,ARRHENIUS LAB,DEPT ORGAN CHEM,S-10691 STOCKHOLM,SWEDEN

[2] LINKOPING UNIV,DEPT CHEM,S-58183 LINKOPING,SWEDEN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 09期

关键词：

D O I：

10.1021/jo00009a012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides is described. (2S,3R)-3-[[(4-Bromobenzyl)oxy]methyl]oxirane-2-methanol (1) was regioselectively alkylated using allylmagnesium bromide. The allyl double bond was oxidatively cleaved, and the product was treated with acidic methanol to give the requisite methyl furanoside derivative 5, which was subsequently condensed with purine and pyrimidine bases. Deblocking and separation of the anomers by chromatography afforded the alpha- and beta-nucleoside analogues.

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页码：2993 / 2997

页数：5

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