Synthesis of [5′-2H1]-nucleosides with defined (5′S)/(5′R)-ratios

被引：7

作者：

Oogo, Y ^{[1
]}

Ono, A ^{[1
]}

Kainosho, M ^{[1
]}

机构：

[1] Tokyo Metropolitan Univ, Fac Sci, Dept Chem, Hachioji, Tokyo 1920397, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(98)00433-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for preparing 5'-monodeuterated nucleosides with defined (S'S)/(5'R)-ratios, starting from glucose, is described. The 5-oxopentose derivatives, derived from glucose, were treated with LiAlD4 in the presence of LiI and/or t-amylalcohol to give stereoselectively 5-monodeuterated pentose derivatives. Using various reaction conditions, the stereoselectivity of the monodeuterated 5-hydroxymethyl group could be partially controlled, in the range of isotopomeric ratios, (5S)/(5R), of 4 : 1 to 1 : 7.4. Using appropriate mixtures of the 5-monodeuterated pentoses with different isotopomeric ratios, we could prepare 5'-monodeuterated nucleosides with defined isotopomeric ratios, which will be useful for NMR studies of oligonucleotides. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2873 / 2876

页数：4

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