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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Doi:10.1055/s-1973-22285
(1973)Doi:10.1016/S0040-4020(03)00472-1
(2003)Doi:10.1021/ja01158a502
(1950)Doi:10.1021/jo00213a040
(1985)Doi:10.1039/c39890001189
(1989)Doi:10.1246/bcsj.40.1709
(1967)