New N-alkylsulfonamides and alkyl sulfonates derived from 6-C-sulfosugars

被引：18

作者：

Ulgar, V ^{[1
]}

Maya, I ^{[1
]}

Fuentes, J ^{[1
]}

Fernández-Bolaños, JG ^{[1
]}

机构：

[1] Univ Sevilla, Fac Quim, Dept Quim Organ, E-41071 Seville, Spain

来源：

TETRAHEDRON | 2002年 / 58卷 / 39期

关键词：

sulfonyl chlorides; sulfonates; sulfonamides; pseudo-disaccharide; phase-transfer catalysis;

D O I：

10.1016/S0040-4020(02)00874-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Protected 6-C-sulfosugars have been transformed into alkyl sulfonates and N-alkylsulfonamides, including a pseudo-disaccharide with a 6 to 6'-sulfonamide linkage. The method involves the oxidation of 6-thioacetate sugar derivatives to 6-C-sulfosugars, and their transformation into sulfonyl chlorides using SO2O2 in anhydrous CH2O2 followed by in situ coupling with nucleophiles in the presence of an excess of base. Sulfonylation through phase-transfer conditions has proved to be suitable for the synthesis of the pseudo-disaccharide. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：7967 / 7973

页数：7

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