From d- to l-Monosaccharide Derivatives via Photodecarboxylation–Alkylation

[Image: see text] Photodecarboxylation–alkylation of conformationally locked monosaccharides leads to inversion of stereochemistry at C5. This allows the synthesis of l-sugars from their readily available d-counterparts. Via this strategy, methyl l-guloside was synthesized from methyl d-mannoside in...

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Detalles Bibliográficos
Autores principales: Wan, I. C. Steven, Witte, Martin D., Minnaard, Adriaan J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6759743/
https://www.ncbi.nlm.nih.gov/pubmed/31512472
http://dx.doi.org/10.1021/acs.orglett.9b03016
Descripción
Sumario:[Image: see text] Photodecarboxylation–alkylation of conformationally locked monosaccharides leads to inversion of stereochemistry at C5. This allows the synthesis of l-sugars from their readily available d-counterparts. Via this strategy, methyl l-guloside was synthesized from methyl d-mannoside in 21% yield over six steps.

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