Synthesis and anti-tumor activity of β-C-glycoside analogs of the immunostimulant KRN7000

被引：26

作者：

Chaulagain, MR

Postema, MHD ^{[1
]}

Valeriote, F

Pietraszkewicz, H

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

[2] Henry Ford Hlth Syst, Dept Internal Med, Josephine Ford Canc Ctr, Div Hematol & Oncol, Detroit, MI 48202 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 41期

基金：

美国国家科学基金会;

关键词：

C-glycoside; olefin; ring-closing metathesis (RCM); KRN7000; ceramide; immunostimulant; anti-tumor;

D O I：

10.1016/j.tetlet.2004.07.163

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A ring-closing metathesis approach was employed for the synthesis of a beta-C-glycoside analog of the immunostimulant KRN7000. The protected Gglycosyl amino acid derivative 18 was converted to amino-olefin 20, and osmylation served to install the diol unit as a mixture of separable syn and anti isomers. Deprotection to the hydroxy-amine 21 was followed by N-acylation and debenzylation to deliver the target compound 5. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：7791 / 7794

页数：4

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