Practical syntheses of optically active carbagalactose and their potential application to the carbocyclic analogues of KRN7000

被引：12
|
作者：
Yu, Seok-Ho [1 ]
Park, Jeong-Ju [1 ]
Chung, Sung-Kee [1 ]
机构：
[1] Pohang Univ Sci & Technol, Dept Chem, Pohang 790784, South Korea
来源：
TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 21期
基金：
新加坡国家研究基金会;
关键词：
D O I：
10.1016/j.tetasy.2006.11.014
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Carba-alpha- and beta-D-galactose derivatives were efficiently prepared from a cyclohex-3-ene-1,2-diol derivative 1. Regioselective inversion of 2-OH, and stereoselective dihydroxylation of I were accomplished to provide a carba-p-D-galactose derivative 6 in a good yield and with a high stereoselectivity. Stereo-inversion of 1-OH of 6 via oxidation/reduction gave carba-beta-D-galactose derivative 12 with a high stereoselectivity. An efficient coupling of carba-alpha-galactose 12 with an aziridine derivative of sphingosine has been demonstrated to give 1-O-carba-alpha-galactosyl sphingosine derivative 14. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3030 / 3036
页数：7
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