Methyl glycosides via Fischer glycosylation: translation from batch microwave to continuous flow processing

Aronow, J.; Stanetty, C.; Baxendale, I.R.; Mihovilovic, M.D.

Abstract

A continuous flow procedure for the synthesis of methyl glycosides (Fischer glycosylation) of various monosaccharides using a heterogenous catalyst has been developed. In-depth analysis of the isomeric composition was undertaken and high consistency with corresponding results observed under microwave heating was obtained. Even in cases where addition of water was needed to achieve homogeneity—a prerequisite for the flow experiments—no detrimental effect on the conversion was found. The scalability was demonstrated on a model case (mannose) and as part of the target-oriented synthesis of d-glycero-d-manno heptose, both performed on multigram scale.

Citation

Aronow, J., Stanetty, C., Baxendale, I., & Mihovilovic, M. (2018). Methyl glycosides via Fischer glycosylation: translation from batch microwave to continuous flow processing. Monatshefte für Chemie - Chemical Monthly, 150, 11-19. https://doi.org/10.1007/s00706-018-2306-8

• Journal Article Type: Article
• Acceptance Date: Sep 25, 2018
• Online Publication Date: Nov 17, 2018
• Publication Date: Nov 17, 2018
• Deposit Date: Oct 8, 2018
• Publicly Available Date: Jan 16, 2019
• Journal: Monatshefte für Chemie - Chemical Monthly
• Print ISSN: 0026-9247
• Electronic ISSN: 1434-4475
• Publisher: Springer
• Peer Reviewed: Peer Reviewed
• Volume: 150
• Pages: 11-19
• DOI: https://doi.org/10.1007/s00706-018-2306-8
• Public URL: https://durham-repository.worktribe.com/output/1317083