Sugar-Pirating as an Enabling Platform for the Synthesis of 4,6-Dideoxyhexoses.
J Am Chem Soc
; 142(20): 9389-9395, 2020 05 20.
Article
em En
| MEDLINE
| ID: mdl-32330028
ABSTRACT
An efficient divergent synthetic strategy that leverages the natural product spectinomycin to access uniquely functionalized monosaccharides is described. Stereoselective 2'- and 3'-reduction of key spectinomycin-derived intermediates enabled facile access to all eight possible 2,3-stereoisomers of 4,6-dideoxyhexoses as well as representative 3,4,6-trideoxysugars and 3,4,6-trideoxy-3-aminohexoses. In addition, the method was applied to the synthesis of two functionalized sugars commonly associated with macrolide antibiotics-the 3-O-alkyl-4,6-dideoxysugar d-chalcose and the 3-N-alkyl-3,4,6-trideoxysugar d-desosamine.
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Base de dados:
MEDLINE
Assunto principal:
Desoxiaçúcares
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article