Journal
ORGANIC LETTERS
Volume 15, Issue 1, Pages 88-91Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol303112y
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Funding
- MRC [G0601746, G902173]
- CRUK [C2075/A9106]
- Medical Research Council [G0601746, G0902173] Funding Source: researchfish
- MRC [G0601746, G0902173] Funding Source: UKRI
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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.
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