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A convenient synthesis for anomeric 2-thioglucobioses, 2-thiokojibiose and 2-thiosophorose
1CNRS, Département de Recherche Fondamentale sur la Matière Condensée/SESAM, Centre d'Etudes de Grenoble, France.
Carbohydrate Research
|February 3, 1994
Abstract:
2-S-alpha-D-Glucopyranosyl-2-thio-D-glucopyranose (2-thiokojibiose, 8) and 2-S-beta-D-glucopyranosyl-2-thio-D-glucopyranose (2-thiosophorose, 14) were conveniently prepared by SN2 reaction of the corresponding anomers of 2,3,4,6-tetra-O-acetyl-1-thio-D-glucopyranose with 1,3,4,6-tetra-O-acetyl-2-O-tri-flyl-beta-D-mannopyranose, followed by a deprotection sequence for the anomeric acetate involving conversion into the 1-propenyl glycosides. Alkaline O-deacetylation was followed by smooth hydrolysis of the propenyl group at pH approximately 2.