Concise and stereospecific synthesis of novel bicyclic dideoxynucleosides as potential antiviral agents

被引：23

作者：

Chao, Q ^{[1
]}

Zhang, JZ ^{[1
]}

Pickering, L ^{[1
]}

Jahnke, TS ^{[1
]}

Nair, V ^{[1
]}

机构：

[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA

来源：

TETRAHEDRON | 1998年 / 54卷 / 13期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4020(98)00061-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel class of dideoxynucleosides containing a bicyclic sugar moiety, structurally related to the natural griseolic acids, was synthesized starting from the stereochemically defined compound, 1,4:3,6-dianhydro-D-glucitol. The key intermediate in the synthesis was a [3.3.0] fused bicyclic glycal. Glycosylation of this compound with nucleobase proceeded both regiospecifically and stereospecifically in the presence of an auxiliary agent, N-iodosuccinamide. Changes in stereochemistry during the synthesis was monitored by optical rotation data and confirmed by both 1D and 2D NMR experiments. The synthetic approach described possesses general usefulness. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3113 / 3124

页数：12

共 22 条

[1] SELECTIVE ALKYLATIONS OF 1,4/3,6-DIANHYDRO-D-GLUCITOL (ISOSORBIDE) [J].