An efficient route to optically active inositol derivatives via the resolution of myo-inositol 1,3,5-orthoformate:: a short synthesis of D-myo-inositol-4-phosphate

被引：15
|
作者：
Sureshan, KM [1 ]
Watanabe, Y [1 ]
机构：
[1] Ehime Univ, Dept Appl Chem, Fac Engn, Matsuyama, Ehime 7908577, Japan
来源：
TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 07期
基金：
日本学术振兴会;
关键词：
D O I：
10.1016/j.tetasy.2004.02.020
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
An efficient method for the resolution of myo-inositol 1,3,5-orthoformate has been developed. The triol, 1 was converted to diastereomers via reaction with (S)-O-acetylmandeloyl chloride. Conditions were optimized for a diastereomeric ratio of 7:3. Both the diastereomers could be separated by column chromatography. The absolute configurations of the diastereomers were determined by converting the less polar diastereomer to the known L-2,4-di-O-benzyl-myo-inositol. The utility of the resolved derivatives is illustrated by a short and efficient synthesis of D-myo-inositol-4-phosphate in four steps from myo-inositol. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1193 / 1198
页数：6
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