Selective acetylation of per-O-TMS-protected monosaccharides

Mark A. Witschi, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticlepeer-review

51 Scopus citations


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
Issue number19
StatePublished - Oct 1 2010

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry


Dive into the research topics of 'Selective acetylation of per-O-TMS-protected monosaccharides'. Together they form a unique fingerprint.

Cite this