Ultrasonic assisted Fischer glycosylation: generating diversity for glycochemistry

Mol Divers. 2011 May;15(2):341-5. doi: 10.1007/s11030-010-9281-2. Epub 2010 Oct 8.

Abstract

In this study ultrasound has been utilised for the Fischer glycosylation using free sugars and sulphuric acid immobilized on silica as catalyst. N-acetyl-D-glucosamine, N-acetyl-D-galactosamine, D-glucose, D-galactose, D-mannose, L-fucose, and lactose were glycosylated with propargyl alcohol or 2-azidoethanol affording the corresponding glycosides, with the production of the α-glycopyranoside as the dominant product. Remarkable acceleration of the glycosylation reactions (15 min-2 h compared to several hours) over reported procedures together with good yields were always observed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biochemistry*
  • Carbohydrate Metabolism / physiology*
  • Glycosylation
  • Ultrasonography*