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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.

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


Authors

C. Stanetty



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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Publisher Licence URL
http://creativecommons.org/licenses/by/4.0/

Copyright Statement
© 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.





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