First Gram-Scale Synthesis of a Heparin-Related Dodecasaccharide

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

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.

Citation

Hansen, S. U., Miller, G. J., Jayson, G. C., & Gardiner, J. M. (2013). First Gram-Scale Synthesis of a Heparin-Related Dodecasaccharide. Organic Letters, 15(1), 88 - 91. https://doi.org/10.1021/ol303112y

• 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