Cyclic Sulfates as Alkylating Agents in Anomeric O-Alkylation of Glucose - Synthesis of New Surfactants

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Abstract
Reaction of cyclic 1,2-sulfates 2a-c with glucose directly furnished sodium 1-(glucopyranosyloxymethyl) alkyl sulfates 3a-c. Their treatment with acid led cleanly to desulfation and gave 2-hydroxyalkyl glucopyranosides 4a-c which exhibit very promising surfactant properties. The structure of these compounds were assigned via the per-O-acetyl derivatives 5a α -5c α and 5a β -5c β .

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