Stereoselective Protection-Free Modification of 3-Keto-saccharides.
Journal
Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393
Informations de publication
Date de publication:
17 07 2020
17 07 2020
Historique:
pubmed:
9
7
2020
medline:
9
7
2020
entrez:
9
7
2020
Statut:
ppublish
Résumé
Unprotected 3-keto-saccharides have become readily accessible via site-selective oxidation, but their protection-free functionalization is relatively unexplored. Here we show that protecting groups are obsolete in a variety of stereoselective modifications of our model substrate methyl α-glucopyranoside. This allows the preparation of rare sugars and the installation of click handles and reactive groups. To showcase the applicability of the methodology, maltoheptaose has been converted into a chemical probe, and the rare sugar evalose has been synthesized.
Identifiants
pubmed: 32635733
doi: 10.1021/acs.orglett.0c01986
pmc: PMC7372562
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
5622-5626Références
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