The Staudinger/aza-Wittig/Grignard reaction as key step for the concise synthesis of 1-C-Alkyl-iminoalditol glycomimetics.
Carbohydr Res
; 429: 62-70, 2016 Jun 24.
Article
em En
| MEDLINE
| ID: mdl-27160850
ABSTRACT
The scope of a one-pot tandem approach for the synthesis of C-1 alkyl iminoalditol derivatives with a Staudinger/aza-Wittig/Grignard cascade has been evaluated. The reaction conditions have been optimized for two azidodeoxy aldose substrates and a range of Grignard reagents. The nature of both, substrate as well as nucleophile, was found to control the stereoselectivity of the alkyl addition to the cyclic iminium intermediate at position C-1. This approach enabled the synthesis of a collection of C-alkyl iminoalditols, which were biologically evaluated as inhibitors against a set of standard glycoside hydrolases. All compounds were found to exhibit highly selective inhibition of ß-glucosidase activity.
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Base de dados:
MEDLINE
Assunto principal:
Álcoois Açúcares
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Beta-Glucosidase
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Inibidores Enzimáticos
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Glicosídeo Hidrolases
Idioma:
En
Ano de publicação:
2016
Tipo de documento:
Article