Synthesis of sphingosine relatives, part 20.: Diastereoselective epoxidation of the double bond at C-4 of sphingosines to provide phytosphingosine relatives such as α-galactosylceramide KRN7000

被引：65

作者：

Takikawa, H ^{[1
]}

Muto, SE ^{[1
]}

Mori, K ^{[1
]}

机构：

[1] Sci Univ Tokyo, Dept Chem, Shinjuku Ku, Tokyo 1620825, Japan

来源：

TETRAHEDRON | 1998年 / 54卷 / 13期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/S0040-4020(98)00065-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselective epoxidation of the double bond at C-4 of two sphingosine derivatives [3, R = (CH2)(7)Me or (CH2)(12)Me] was studied. Dimethyldioxirane was found to be the best oxidant for that purpose. Application of this epoxidation resulted in a new synthesis of the alpha-galactosylceramide KRN7000 (2), which has an enhancing effect on the activity of natural killer cells. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3141 / 3150

页数：10

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