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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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
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author Wan, I. C. Steven
Witte, Martin D.
Minnaard, Adriaan J.
author_facet Wan, I. C. Steven
Witte, Martin D.
Minnaard, Adriaan J.
author_sort Wan, I. C. Steven
collection PubMed
description [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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spelling pubmed-67597432019-09-26 From d- to l-Monosaccharide Derivatives via Photodecarboxylation–Alkylation Wan, I. C. Steven Witte, Martin D. Minnaard, Adriaan J. Org Lett [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. American Chemical Society 2019-09-12 2019-09-20 /pmc/articles/PMC6759743/ /pubmed/31512472 http://dx.doi.org/10.1021/acs.orglett.9b03016 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Wan, I. C. Steven
Witte, Martin D.
Minnaard, Adriaan J.
From d- to l-Monosaccharide Derivatives via Photodecarboxylation–Alkylation
title From d- to l-Monosaccharide Derivatives via Photodecarboxylation–Alkylation
title_full From d- to l-Monosaccharide Derivatives via Photodecarboxylation–Alkylation
title_fullStr From d- to l-Monosaccharide Derivatives via Photodecarboxylation–Alkylation
title_full_unstemmed From d- to l-Monosaccharide Derivatives via Photodecarboxylation–Alkylation
title_short From d- to l-Monosaccharide Derivatives via Photodecarboxylation–Alkylation
title_sort from d- to l-monosaccharide derivatives via photodecarboxylation–alkylation
url 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
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