Synthesis of protected D-altritol nucleosides as building blocks for oligonucleotide synthesis

被引：34

作者：

Allart, B ^{[1
]}

Busson, R ^{[1
]}

Rozenski, J ^{[1
]}

Van Aerschot, A ^{[1
]}

Herdewijn, P ^{[1
]}

机构：

[1] Katholieke Univ Leuven, Rega Inst Med Res, Med Chem Lab, B-3000 Louvain, Belgium

来源：

TETRAHEDRON | 1999年 / 55卷 / 21期

关键词：

D O I：

10.1016/S0040-4020(99)00287-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

D-Altritol nucleosides with an adenine and uracil base moiety were obtained by nucleophilic opening of the epoxide ring of 1,5:2,3-dianhydro-4,6-O-benzylidene-D-allitol using the sodium salt of the above mentioned bases. The use of a 2-trimethylsilylethyl protecting group for the O-6-function of the guanine base offers a useful compromise between stability and acceptable alkylation yields of the N-9-position if the guanine base. The cytosine nucleoside was synthesized starting from the uracil congener. The 3'-hydroxyl function was protected with a benzoyl group. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：6527 / 6546

页数：20

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