ALKYLGLYCOSIDE CARBONATES OF 3'-AZIDO-3'-DEOXYTHYMIDINE

被引：13

作者：

POCHET, S ^{[1
]}

KANSAL, V ^{[1
]}

DESTOUESSE, F ^{[1
]}

SARFATI, SR ^{[1
]}

机构：

[1] INST PASTEUR,CNRS,UNITE ONCOL VIRALE,F-75724 PARIS 15,FRANCE

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(00)98018-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Analogues of 3′-azido-3′-deoxythymidine (AZT) were synthesized by coupling glycosides and AZT through a carbonate bridge. The glycosides were prepared by treatment of 6-benzyloxy-1-hexanol (1) with 2-methyl-3,4,6-tri-Oacetyl-1,2-dideoxy-α-D-glucopyrano-[2,1-d]-2-oxazoline (2) and tetra-O-benzoyl-αD-mannopyranosyl bromide (3), followed by O-deprotection, persilylation and catalytic hydrogenolysis to give the alcohols 10 and 11, respectively. Condensation of 10 and 11 with AZT in the presence of 1,1′-carbonyldiimidazole, followed by removal of the silyl groups, afforded the title compounds. © 1990.

引用

页码：6021 / 6024

页数：4

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