Effect of the C-2 hydroxyl group on the mesomorphism of alkyl glycosides: synthesis and thermotropic behavior of alkyl 2-deoxy-D-arabino-hexopyranosides

Singh, Madan Kumar and Jayaraman, Narayanaswamy and Rao, DS Shankar and Prasad, S Krishna (2008) Effect of the C-2 hydroxyl group on the mesomorphism of alkyl glycosides: synthesis and thermotropic behavior of alkyl 2-deoxy-D-arabino-hexopyranosides. In: Chemistry and Physics of Lipids, 155 (2). pp. 90-97.

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Abstract

A homologous series of alkyl 2-deoxy-alpha-D-arabino-hexopyranosides and alkyl 2-deoxy-beta-D-arabino-hexopyranosides were synthesized, upon glycosylation of 1-alkanols (from C-8 to C-18 alkanols) with ethyl 2-deoxy-3,4,6-tri-O-acetyl-1-thio-D-arabino-hexopyranoside, followed by a deprotection. The thermotropic behavior of these new types of alkyl glycosides was investigated. It was observed that the beta-anomers of these alkyl glycosides, bearing nonyl to tetradecyl alkyl chain are mesomorphic, exhibiting monotropic smectic A phase. In contrast, the alpha-anomers are all non-mesomorphic. An effort to identify the liquid crystalline behavior of binary mixtures of the alpha- and beta-anomers was undertaken and it was found that mixtures containing equimolar amounts of the anomers exhibited rnesomorphic behavior. A fine balance of the hydrophilic and hydrophobic components within the molecule is also found to be important for the alkyl 2-deoxy glycosides to form the mesophase.

Item Type:	Journal Article
Publication:	Chemistry and Physics of Lipids
Publisher:	Elsevier Science
Additional Information:	Copyright of this article belongs to Elsevier Science.
Keywords:	2-Deoxy glycosides;Glycolipids;Glycosylations;Liquid crystals;Mesophase behavior;Smectic A phase.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	30 Apr 2009 05:23
Last Modified:	19 Sep 2010 04:58
URI:	http://eprints.iisc.ac.in/id/eprint/17688

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