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.

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
• Public URL: https://durham-repository.worktribe.com/output/1439114