Regiospecific Synthesis of New Methyl Sulfoglucopyranoside-Based Surfactants: Nucleophilic Displacement of a Cyclic Sulfate

Hélène G. Bazin; Robert J. Linhardt

doi:10.1055/s-1999-3432

Synthesis 1999; 1999(4): 621-624
DOI: 10.1055/s-1999-3432

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Regiospecific Synthesis of New Methyl Sulfoglucopyranoside-Based Surfactants: Nucleophilic Displacement of a Cyclic Sulfate

Hélène G. Bazin^* , Robert J. Linhardt

^*Division of Medicinal and Natural Products Chemistry and Department of Chemical and Biochemical Engineering, PHAR S328, University of Iowa, Iowa City, IA, 52242, USA; Fax +1(3 19)3 35 66 34; E-mail: robert-linhardt@uiowa.edu

Abstract

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A two-step regiospecific synthesis of a new class of anionic and amphoteric methyl α-d-glucopyranoside-based surfactants is described. Reaction of methyl α-d-glucopyranoside with thionyl chloride followed by oxidation of the resulting sulfite afforded the corresponding methyl α-d-glucopyranoside 4,6-cyclic sulfate in high yield. Nucleophilic displacement of this cyclic sulfate by different fatty acids and amines led to the corresponding methyl 6-O-acyl- or 6-amino-6-deoxy-4-sulfoglucopyranosides in very good yields. These newly synthesized sulfoglucopyranoside-based surfactants displayed low critical micelle concentration (CMC) values.

cyclic sulfates - anionic surfactants - amphoteric surfactants

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