Allylsilanes in the preparation of 5′-C-hydroxy or bromo alkylthymidines

被引：26

作者：

Banuls, V ^{[1
]}

Escudier, JM ^{[1
]}

机构：

[1] Univ Toulouse 3, CNRS, F-31062 Toulouse 4, France

来源：

TETRAHEDRON | 1999年 / 55卷 / 18期

关键词：

allylation; rearrangement; diastereoselection; 5 '-C-substituted-nucleosides;

D O I：

10.1016/S0040-4020(99)00246-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 5'-C-thymidine aldehyde with allytrimethylsilane promoted by BF3:Et2O lead stereoselectively to 5'-C(S)-allylthymidine which is converted to 5'-C(S) C(S)-hydroxyhexylthymidine. 5'-C-(R or S) hydroxypentylthymidine can be obtained by using omega-tertButyldimethylsilyloxyallyltrimethylsilane in the Sakurai reaction. In the same conditions, omega-Bromoallyltrimethylsilane adds to the aldehyde with a complete transposition of the siliranium intermediate and allows the preparation of the 5'-C(S)-bromopentene derivative, (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5831 / 5838

页数：8

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