Process for preparing alkyl-1-thioglycosides and alkyl-glycoside

Details Process for preparing alkyl-1-thioglycosides and alkyl-glycoside Process for preparing alkyl-1-thioglycosides and alkyl-glycoside

1990-07-31

1992-06-02

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 185, 536 186, 536 175, 536122, 536124, C07H 100, C07H 1500

Patent

active

051188040

ABSTRACT:
A process for preparing alkykl-1-thio-.alpha.,.beta.-glycosides and alkyl glycosides is described. The glycosides are prepared from a saccharide selected from monosaccharides and reducible di- and oligo-saccharides. The saccharide is reacted with either a thiol to produce an alkyl-1-thio-.alpha.,.beta.-glycoside or an alcohol to produce an alkyl glycoside in the presence of the solvent and reagent poly-(hydrogen fluoride)-pyridinium. Novel alkyl-1-thio-.alpha.,.beta.-glycosides prepared by the process of the invention are characterized in that they are in the form of a mixture of .alpha. and .beta. anomers. The alkyl-1-thio-.alpha.,.beta.-glycosides having a long alkyl chain are useful as nonionic detergents, in particular in the extraction of membrane proteins.

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