First gram-scale synthesis of a heparin-related dodecasaccharide

Org Lett. 2013 Jan 4;15(1):88-91. doi: 10.1021/ol303112y. Epub 2012 Dec 14.

Abstract

The first example of a gram-scale synthesis of a structurally defined, heparin-related dodecasaccharide is reported. An iterative 14-step process using an iduronate donor disaccharide delivers >1g quantities of the dodecasaccharide sequence [GlcNS-IdoA2S](6)-OMe in 15% overall yield from the reducing terminal disaccharide, a 2 orders of magnitude increase in scale for access to synthetic heparanoid dodecasaccharide mimetics. The synthesis also delivers multigram amounts of the protected oligosaccharides from tetra- through to dodecasaccharide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Heparin / chemistry*
  • Iduronic Acid / chemistry
  • Molecular Structure
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Oligosaccharides
  • Iduronic Acid
  • Heparin