Carbohydrate Research p. 423 - 434 (1997)
Update date:2022-08-25
Topics:
Galema, Saskia A.
Engberts, Jan B. F. N.
Van Doren, Henk A.
This paper describes the synthesis, purification, and liquid- crystalline behaviour of a series of alkyl 1-thioglycopyranosides. The synthesis of these derivatives was carried out via a Lewis acid mediated coupling of the fully acetylated monosaccharide with an alkanethiol. The choice of the Lewis acid depends on the configuration of AcO-2. The carbohydrate-derived surfactants exhibit thermotropic liquid-crystalline behaviour. The alkyl 1-thioglycopyranosides form the expected smectic A phases upon heating. The clearing temperatures vary with alkyl chain length which is in accordance with the accepted model for the S(A) phase of amphiphilic carbohydrate mesogens. For the alkyl 1-thiotalopyranosides, the clearing points are much lower than expected, presumably due to the formation of an intramolecular hydrogen bond in the talose moiety.
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