Skip to main content

Research Repository

Advanced Search

First Gram-Scale Synthesis of a Heparin-Related Dodecasaccharide

Hansen, Steen U.; Miller, Gavin J.; Jayson, Gordon C.; Gardiner, John M.

Authors

Steen U. Hansen

Gordon C. Jayson

John M. Gardiner



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.

Journal Article Type Article
Online Publication Date Dec 14, 2012
Publication Date Jan 4, 2013
Journal Organic Letters
Print ISSN 1523-7060
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 15
Issue 1
Pages 88 - 91
DOI https://doi.org/10.1021/ol303112y
Publisher URL http://pubs.acs.org/doi/abs/10.1021/ol303112y