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
收藏
页码：7791 / 7794
页数：4
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