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ChemInform Abstract: Synthesis, Purification and Liquid-Crystalline Behavior of Several Alkyl 1-Thio-D-glycopyranosides.

✍ Scribed by S. A. GALEMA; J. B. F. N. ENGBERTS; H. A. VAN DOREN

Publisher: John Wiley and Sons
Year: 2010
Weight: 35 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199808189

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✦ Synopsis

Synthesis, Purification and Liquid-Crystalline Behavior of Several Alkyl 1-Thio-D-glycopyranosides.

-The synthesis of the title compounds is achieved via Lewis acid mediated coupling of the fully acetylated monosaccharide with the appropriate alkanethiol. The choice of the Lewis acid depends on the configuration of the monosaccharide at C-2. The carbohydratederived surfactants (IV), (VII), and (X) exhibit thermotropic liquid-cystalline behavior and form smectic A phases upon heating. Clearing points increase with longer chain length. For talose derivatives such as (X), clearing points are much lower than expected, presumably due to the formation of an intramolecular hydrogen bond in the talose moiety. -(GALEMA, S. A.; ENGBERTS, J.

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