Selective acetylation of per-O-TMS-protected monosaccharides

Mark A. Witschi, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

44 Scopus citations

Abstract

Figure Presented. Selective acetylation of various per-O-TMS-protected carbohydrates has been accomplished. Using a protecting group exchange strategy and microwave assistance, monosaccharides (glucose, galactose, and mannose) can be selectively acetylated producing either the 6-O-monoacetate or 1,6-O-diacetylated species. This new class of molecules can be deprotected without migration of the acetyl groups, providing useful synthetic intermediates. To demonstrate the scope of the reaction, the methodology was successfully extended to TMS-protected ceramide.

Original languageEnglish (US)
Pages (from-to)4312-4315
Number of pages4
JournalOrganic Letters
Volume12
Issue number19
DOIs
StatePublished - Oct 1 2010

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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