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Synlett 1990; 1990(10): 631-632
DOI: 10.1055/s-1990-21193
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A New Activating Principle in Glycoside Synthesis Based on Electrophile-Induced Lactonization of Glucosyl 4-Pentenoates

Horst Kunz* , Peter Wernig, Michael Schultz
  • *Institut für Organische Chemie der Universität Mainz, Becherweg 18-20, D-6500 Mainz, Federal Republic of Germany
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Publication Date:
08 March 2002 (online)

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After activation with soft electrophiles, e.g. iodonium compounds or 1,3-dithian-2-ylium tetrafluoroborate, O-benzyl-, O-acyl- and N-acyl-protected glycosyl 4-pentenoates 2, prepared by the condensation of the corresponding glucopyranoses 1 with 4-pentenoic acid using diisopropylcarbodiimide, react with alcohols to give the corresponding glycosides 3. This glycosylation proceeds as an electrophile-induced lactonization during which the γ-lactones 4 are formed as the leaving groups at the anomeric center.