Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa-O-acetyl-l-glycero-α-d-manno-heptopyranose.
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Publication Date
2015-04Journal Title
European J Org Chem
ISSN
1434-193X
Publisher
Wiley
Volume
2015
Issue
12
Pages
2718-2726
Language
eng
Type
Article
This Version
VoR
Physical Medium
Print-Electronic
Metadata
Show full item recordCitation
Stanetty, C., & Baxendale, I. R. (2015). Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa-O-acetyl-l-glycero-α-d-manno-heptopyranose.. European J Org Chem, 2015 (12), 2718-2726. https://doi.org/10.1002/ejoc.201500024
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.
Identifiers
External DOI: https://doi.org/10.1002/ejoc.201500024
This record's URL: https://www.repository.cam.ac.uk/handle/1810/287239
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