Immunomodulating glycosphingolipids:: an efficient synthesis of a 2′-deoxy-α-galactosyl-GSL

被引：25

作者：

Costantino, V ^{[1
]}

Fattorusso, E ^{[1
]}

Imperatore, C ^{[1
]}

Mangoni, A ^{[1
]}

机构：

[1] Univ Naples Federico II, Dipartimento Chim Sostanze Nat, I-80131 Naples, Italy

来源：

TETRAHEDRON | 2002年 / 58卷 / 02期

关键词：

galactal; alpha-glycosidation; glycosphingolipids; immunomodulating;

D O I：

10.1016/S0040-4020(01)01163-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and efficient approach to the total synthesis of 2'-deoxy-alpha-galactosyl glycosphingolipids was accomplished. Commercially available 3,4,6-tri-O-acetylgalactal was used as the chiral starting material for both the sugar and phytosphingosine building blocks required for the synthesis of 1-O-(2-deoxy-alpha-D-galactopyranosyl)-2-docosanoylamino-1,3,4-octadecanetriol. The key step of the synthetic strategy was the stereoselective alpha-glycosidation of the azido precursor of sphingosine. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：369 / 375

页数：7

共 10 条

[1] The Wittig reaction with 2-deoxysugars: the role of triphenyl and trialkyltin halides [J].