Indium triflate catalyzed peracetylation of carbohydrates

Carbohydr Res. 2008 Jul 21;343(10-11):1814-8. doi: 10.1016/j.carres.2008.04.009. Epub 2008 Apr 10.

Abstract

Peracetylation is a very common protection strategy that is widely implemented in carbohydrate synthesis. Here, a method for the peracetylation of carbohydrates using catalytic In(OTf)(3) in neat acetic anhydride is reported. In(OTf)(3) has low toxicity and is mild and water tolerant, and the reactions are high yielding and efficient. Details regarding the scope and mechanism of the reaction are briefly discussed.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acetylation*
  • Carbohydrates / chemistry*
  • Carbohydrates / radiation effects
  • Catalysis
  • Indium / chemistry*
  • Mesylates / chemistry*
  • Microwaves
  • Solubility

Substances

  • Carbohydrates
  • Mesylates
  • Indium
  • trifluoromethanesulfonic acid