Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose

Stanetty, C.; Baxendale, I.R.

doi:10.1002/ejoc.201500024

Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose

Stanetty, C.; Baxendale, I.R.

Authors

C. Stanetty

Professor Ian Baxendale i.r.baxendale@durham.ac.uk
Professor

Abstract

The higher-carbon sugar l-glycero-d-manno-heptose is a major constituent of the inner core region of the lipopolysaccharide (LPS) of many Gram-negative bacteria. All preparative routes used to date require multiple steps, and scalability has been rarely addressed. Here a highly practical synthesis of crystalline 1,2,3,4,6,7-hexa-O-acetyl-l-glycero-α-d-manno-heptopyranose by a simple four-step sequence starting from l-lyxose is disclosed. Only two recrystallisations are required and the process was demonstrated on a >100 mmol scale, yielding 41 g of the target compound.

Citation

Stanetty, C., & Baxendale, I. (2015). Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose. European Journal of Organic Chemistry, 2015(12), 2718-2726. https://doi.org/10.1002/ejoc.201500024

Journal Article Type	Article
Online Publication Date	Mar 10, 2015
Publication Date	Apr 1, 2015
Deposit Date	May 4, 2015
Publicly Available Date	Apr 21, 2016
Journal	European Journal of Organic Chemistry
Print ISSN	1434-193X
Electronic ISSN	1099-0690
Publisher	Wiley
Peer Reviewed	Peer Reviewed
Volume	2015
Issue	12
Pages	2718-2726
DOI	https://doi.org/10.1002/ejoc.201500024

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© 2015 The Authors. Published by WILEY-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.