Spiro-sulfamidate and sulfate nucleosides via 2′ and 3′-C-branched-chain sugars and nucleosides

被引：8

作者：

Lalot, Jerome ^{[1
]}

Tite, Tony ^{[1
]}

Wadouachi, Anne ^{[1
]}

Postel, Denis ^{[1
]}

Van Nhien, Albert Nguyen ^{[1
]}

机构：

[1] Univ Picardie Jules Verne, Lab Glucides, UMR6219, Fac Sci, F-80039 Amiens, France

来源：

TETRAHEDRON | 2011年 / 67卷 / 33期

关键词：

3 '-C-Nucleoside; 1,3-Diol; Spiro-sulfate; Sulfamidate; Carbohydrate; Burgess reagent; ACID RELATED-COMPOUNDS; CYCLIC SULFATES; STEREOSELECTIVE-SYNTHESIS; BURGESS REAGENT; DERIVATIVES; NUCLEOTIDES; URACIL; 3'-KETONUCLEOSIDES; POLYMERASE; PROTECTION;

D O I：

10.1016/j.tet.2011.06.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

C-branched-chain sugars and nucleosides were obtained by organocatalysis from ulose derivatives. After a reduction step, the corresponding 1,3-diol was derivatized into 3'-spiro-sulfamidates and unexpected sulfates by treatment with a Burgess reagent. Deprotection of the Boc-derivatives was carried out while preserving the cyclic sulfate. An example of ring opening of the cyclic sulfate derivative with sodium azide leading to the corresponding 3'-C-azidoalkyl branched-chain nucleosides is given. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6006 / 6017

页数：12

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