First gram-scale synthesis of a heparin-related dodecasaccharide

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

doi:10.1021/ol303112y

First gram-scale synthesis of a heparin-related dodecasaccharide

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

Research output: Contribution to journal › Article › peer-review

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. © 2012 American Chemical Society.

Original language	English
Pages (from-to)	88-91
Number of pages	3
Journal	Organic Letters
Volume	15
Issue number	1
DOIs	https://doi.org/10.1021/ol303112y
Publication status	Published - 4 Jan 2013

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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. {\textcopyright} 2012 American Chemical Society.",

author = "Hansen, {Steen U.} and Miller, {Gavin J.} and Jayson, {Gordon C.} and Gardiner, {John M.}",

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AB - 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. © 2012 American Chemical Society.

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First gram-scale synthesis of a heparin-related dodecasaccharide

Abstract

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