Masked Thiol Sugars: Chemical Behavior and Synthetic Applications of S??Glycopyranosyl??N??monoalkyl Dithiocarbamates

…, J Parada??Aliste, FJ Lopez??Jaramillo…

Index: Megia-Fernandez, Alicia; De La Torre-Gonzalez, Diego; Parada-Aliste, Jose; Lopez-Jaramillo, Francisco Javier; Hernandez-Mateo, Fernando; Santoyo-Gonzalez, Francisco Chemistry - An Asian Journal, 2014 , vol. 9, # 2 p. 620 - 631

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Abstract

Abstract The chemical behavior of S-glycopyranosyl-N-monoalkyl dithiocarbamates (DTCs) as masked 1-glycosyl thiols, easily prepared by the nucleophilic displacement of 1-halo sugars with dithiocarbamate salts of primary amines, has been studied and synthetically exploited. This behavior relies on the abstraction of the proton of the carbamate functionality that allows controlled access to thiolate sugar intermediates. The basic character of the ...