Synthesis of pseudonucleosides containing chiral sulfahydantoins as aglycone (II)

被引：36

作者：

Dewynter, G

Aouf, N

Regainia, Z

Montero, JL

机构：

[1] Lab. de Chimie Biomoléculaire, CC-073 Univ. Montpellier II -Sci. T., 34 095 Montpellier Cedex 05, Pl. E. Bataillon

[2] Institut de Chimie, Université de Annaba, El Hadjar

来源：

TETRAHEDRON | 1996年 / 52卷 / 03期

关键词：

chlorosulfonyl isocyanate; amino acids; carboxylsulfamide; Mitsunobu reaction; sulfahydantoin; thiadiazolidinone dioxide; glycosylation; pseudonucleoside;

D O I：

10.1016/0040-4020(95)00932-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of chiral sulfahydantoins have been synthesized by alkaline cyclization starting from N-sulfamylaminoacid methyl esters. Regioselective glycosylation of these pseudopyrimidic heterocycles was carried out with a benzyl protecting group on the N-sulfonylcarbamic position. Best glycosylation results were obtained by preliminary silylation of sulfahydantoins, and their condensation with a tetracylribofuranose which yielded the pseudonucleosides in a beta-anomeric configuration.

引用

页码：993 / 1004

页数：12

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