Versatile acetylation of carbohydrate substrates with bench-top sulfonic acids and application to one-pot syntheses of peracetylated thioglycosides

Chin Sheng Chao, Min Chun Chen, Shih Che Lin, Kwok-Kong Mong*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

Inexpensive and readily available sulfonic acids, p-toluenesulfonic acid, and sulfuric acid are versatile and efficient catalysts for the peracetylation of a broad spectrum of carbohydrate substrates in good yield and in a practical time frame. Three appealing features in sulfonic acid-catalyzed acetylation of free sugars were explored including (1) suppression of furanosyl acetate formation for d-galactose and l-fucose; (2) high yielding chemoselective acetylation of sialic acid under appropriate conditions; and (3) peracetylation of amino sugars with different amino protecting functions. Simple one-pot two step acetylation-thioglycosidation methods for the expeditious synthesis of p-tolyl per-O-acetyl thioglycosides were also delineated.

Original languageEnglish
Pages (from-to)957-964
Number of pages8
JournalCarbohydrate Research
Volume343
Issue number5
DOIs
StatePublished - 7 Apr 2008

Keywords

  • Acid-catalyzed acetylation
  • Amino sugars
  • One-pot protecting group manipulation
  • p-Toluenesulfonic acid

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