Molbank (Sep 2024)

Thiazolylketol Acetates as Glycosyl Donors: Stereoselective Synthesis of a <i>C</i>-Ketoside

  • Clark Ferrari,
  • Alessandro Dondoni,
  • Alberto Marra

DOI
https://doi.org/10.3390/M1883
Journal volume & issue
Vol. 2024, no. 3
p. M1883

Abstract

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We have already proven that thiazolylketol acetates, synthetised by addition of 2-lithiothiazole to sugar lactones followed by acetylation, are efficient glycosyl donors in the presence of O-, N-, and P-nucleophiles. We describe here their first use in the C-glycosidation using trimetylsilyl cyanide as the acceptor in order to prepare, after thiazole-to-formyl unmasking and reduction, the corresponding C-ketosides.

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