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

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 unde...

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Detalles Bibliográficos
Autores principales: Aronow, Jonas, Stanetty, Christian, Baxendale, Ian R., Mihovilovic, Marko D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2018
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6320746/
https://www.ncbi.nlm.nih.gov/pubmed/30662091
http://dx.doi.org/10.1007/s00706-018-2306-8
Descripción
Sumario: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. GRAPHICAL ABSTRACT: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s00706-018-2306-8) contains supplementary material, which is available to authorized users.

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