Tandem one-pot acetalation-acetylation for direct access to differentially protected thioglycosides and O-glycosides with p-toluenesulfonic acid

Kwok-Kong Mong, Chin Sheng Chao, Min Chun Chen, Chun Wei Lin

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

A new tandem one-pot acetalation-acetylation procedure is reported which streamlines routine protecting-group manipulation of carbohydrate molecules in production of differentially protected O- and thioglycosides. This new procedure eliminates the use of highly toxic pyridine, and p-toluenesulfonic acid is employed as catalyst for acetalation and acetylation. Synthetic utility of the new procedure is demonstrated in the expeditious preparation of differentially protected glycosides from a wide variety of carbohydrate substrates including unprotected O-glycosides, thioglycosides, and N-acetyl neuraminic acid ester.

Original languageEnglish
Pages (from-to)603-606
Number of pages4
JournalSynlett
Issue number4
DOIs
StatePublished - 1 Mar 2009

Keywords

  • Acetals
  • Glycosides
  • Oligosaccharides
  • Protecting group
  • Tandem

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