Stereoselective synthesis of L-isoxazolidinyl thymidine from N-benzyl-1,2-di-O-isopropylidene-D-glyceraldehyde nitrone (BIGN)

被引：36

作者：

Merino, P ^{[1
]}

del Alamo, EM ^{[1
]}

Franco, S ^{[1
]}

Merchan, FL ^{[1
]}

Simon, A ^{[1
]}

Tejero, T ^{[1
]}

机构：

[1] Univ Zaragoza, Fac Ciencias, ICMA, Dept Quim Organ, E-50009 Zaragoza, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(00)00094-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A synthetic approach to L-isoxazolidinyl nucleosides is demonstrated by the stereoselective conversion of N-benzyl-1,2-di-O-isopropylidene-D-glyceraldehyde nitrone (BIGN) into cis and trans L-isoxazolidinyl thymidine. The methodology consists of the 1,3-dipolar cycloaddition of BIGN with either vinyl acetate or a vinyl base to give key intermediates that are easily transformed into the target compound. The experimental results of the cycloaddition reactions can be qualitatively explained by theoretical ab initio calculations. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1543 / 1554

页数：12

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