POSSIBLE MODEL FOR A NEW CHIRAL GLYCERIDE SYNTHESIS .1. SYNTHESIS OF 1-O-AROYL-2-O-TOSYL-SN-GLYCEROLS

被引:25
作者
MORPAIN, C
TISSERAND, M
机构
[1] Institut de Chimie, Université de Besançon
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 06期
关键词
D O I
10.1039/p19790001379
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A procedure has been developed which permits the synthesis of mixed-acid 1,2-di-O-aroyl-sn-glycerols via 1,6-di-O-aroyl-2,5-di-O-tosyl-D-mannitol. The method was applied to the synthesis of some (S)-(+)-1-O-aroyl-2-O-tosyl-sn- glycerols. In order to check the structure and the optical purity of the 1,2-diglycerides, tritylation to give 3-trityl ethers was carried out. 1-Trityl ethers were prepared by a second method via 3-O-aroyl-sn-glycerols. The optical rotations of the 3- and 1-trityl ethers were compared. Oxidation of 1,6-di-O-aroyl-2,5-di-O-tosyl-D-mannitol at temperatures above 25 °C took place with complete or partial racemisation.
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页码:1379 / 1383
页数:5
相关论文
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[12]  
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