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Synthesis and Thermotropic Behavior of Simple New Glucolipid Amides
Authors:Stéphane Chambert  Alain Doutheau  Stephen J. Cowling  John W. Goodby  Grahame Mackenzie
Affiliation:1. Laboratoire de Chimie Organique , Université Lyon 1, INSA‐Lyon, CPE‐Lyon;2. Institut National des Sciences Appliquées de Lyon , Villeurbanne, France;3. Department of Chemistry , The University of York , York, UK;4. Department of Chemistry , The University of Hull , Hull, UK
Abstract:

The coupling reaction of 3,4,6‐tri‐O‐acetyl‐α‐d‐glucopyranoside 2‐O‐lactone 1 (α‐CMGL) with two kinds of lipophilic amines, aminosteroids and fatty amines, efficiently yielded, after deprotection, the corresponding free α‐glucolipid amides. The latter family of compounds exhibited good thermal stability, allowing the higher homologs having longer linear fatty chains or saturated steroids to possess lamellar smectic A phases.
Keywords:Liquid crystals  Steroids  Glycolipids  Carbohydrate  Carboxylmethyl, Glycoside
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