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Synthesis 1996; 1996(6): 687-689
DOI: 10.1055/s-1996-4279
short paper
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Cyclic Sulfates as Alkylating Agents in Anomeric O-Alkylation of Glucose - Synthesis of New Surfactants

Wolfgang Klotz, Richard R. Schmidt*
  • *Fakultät Chemie, Universität Konstanz, Postfach 5560 M 725, D-78434 Konstanz, Germany, Fax +49(7531)883135
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Publikationsdatum:
31. Dezember 2000 (online)

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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 .

cyclic 1,2-sulfates - desulfation - surfactants - sodium 1-(glucopyranosyloxymethyl) alkyl sulfates - 2-hydroxyalkyl glycopyranosides