A concise synthesis of (3S,4S,5R)-1-(α-D-galactopyranosyl)-3-tetracosanoylamino-4,5-decanediol, a C-glycoside analogue of immunomodulating α-galactosylceramide OCH

被引：28

作者：

Toba, T

Murata, K

Yamamura, T

Miyake, S

Annoura, H

机构：

[1] Daiichi Suntory Pharma Co Ltd, Biomed Res Labs, Osaka 6188513, Japan

[2] Natl Inst Neurosci, NCNP, Dept Immunol, Tokyo 1878502, Japan

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 30期

关键词：

C-glycoside; OCH; ceramide; CD1d; NKT cell ligand;

D O I：

10.1016/j.tetlet.2005.05.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and convergent synthesis of the C-glycoside analogue 2b of immunomodulating alpha-galactosylceramide OCH 1b starting from readily available 2,3,4,6-tetra-O-bensyl-D-galactose 3 and L-arabinose 6 is described. The synthesis features the nucleophilic addition of an alpha-ethynyl sugar 5 to the phytosphingosine-precursor aldehyde 9 and would be applicable to a variety of C-glycoside analogues of interest. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：5043 / 5047

页数：5

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