Synthesis of 1,2-O-isopropylidene-3,5-O-propylidene-α-D-glucofuranose as a convenient precursor of both 6-O-alkyl and 6-O-glycidyl-D-glucose amphiphiles

被引：11
|
作者：
Vanbaelinghem, L [1 ]
Godé, P [1 ]
Goethals, G [1 ]
Martin, P [1 ]
Ronco, G [1 ]
Villa, P [1 ]
机构：
[1] Univ Picardie, Lab Chim Organ & Cinet, F-80039 Amiens, France
来源：
CARBOHYDRATE RESEARCH | 1998年 / 311卷 / 1-2期
关键词：
allyl isomerisation; 1,2-O-isopropylidene-3,5-O-propylidene-alpha-D-glucofuranose; 6-O-alkyl-D-glucose; 6-O-glycidyl-D-glucose; CMC; liquid crystal;
D O I：
10.1016/S0008-6215(98)00207-9
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
1,2-O-Isopropylidene-3,5-O-propylidene-alpha-D-glucofuranose (3) was synthesized by conversion of 3-O-allyl-1,2-O-isopropylidene-alpha-D-glucofuranose (1) into its 3-O-prop-1-enyl isomer (2), followed by rapid acid-catalysed intramolecular acetalation in an aprotic solvent. The diacetal 3 was used as the precursor of 6-O-alkyl and 6-O-glucidyl-D-glucose amphiphiles, which show thermotropic and lyotropic liquid-crystalline properties. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：89 / 94
页数：6
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