Cap-and-tag solid phase oligosaccharide synthesis

J Org Chem. 2008 Mar 21;73(6):2058-65. doi: 10.1021/jo701349c. Epub 2007 Oct 23.

Abstract

A new "cap-and-tag" strategy is applied to solid phase oligosaccharide synthesis. Acetyl-capping and fluorous-tagging allowed for the facile separation of the desired F-tagged oligosaccharide from the acetyl-capped deletion sequences using fluorous solid phase extraction. To illustrate this approach, a protected Glc-beta-(1-->6)-Man-alpha-(1-->6)-Glc-beta-1-->pentenyl trisaccharide was synthesized.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Carbohydrate Sequence
  • Glucose / chemistry
  • Glycosides / chemical synthesis
  • Glycosylation
  • Mannose / chemistry
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis*

Substances

  • Glycosides
  • Oligosaccharides
  • Glucose
  • Mannose