First O-glycosylation of hydroxamic acids.

Thomas, Mickaël; Gesson, Jean-Pierre; Papot, Sébastien

Thomas, Mickaël; Gesson, Jean-Pierre; Papot, Sébastien.

Afiliación

Thomas M; UMR 6514, Synthèse et Réactivité des Substances Naturelles, Université de Poitiers et CNRS, 40, Av. du Recteur Pineau, 86022 Poitiers, France.

J Org Chem ; 72(11): 4262-4, 2007 May 25.

Article en En | MEDLINE | ID: mdl-17465568

RESUMEN

The first O-glycosylation of hydroxamic acids is reported. This process involves the use of glycosyl N-phenyl trifluoroacetimidates as glycosyl donors in the presence TMSOTf and 4 A molecular sieves in dichloromethane. Under such conditions, a wide range of new glycosyl donors including glucosyl, galactosyl, mannosyl, glucuronyl, and ribosyl hydroxamates were prepared in good to high yields. This procedure appears to be an advantageous alternative for the synthesis of glycosyl hydroxamates of biological interest.

Asunto(s)

Fluoroacetatos; Ácidos Hidroxámicos/química; Acetamidas; Conformación de Carbohidratos; Glicosilación; Estructura Molecular; Ácido Trifluoroacético/química

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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Fluoroacetatos / Ácidos Hidroxámicos Idioma: En Revista: J Org Chem Año: 2007 Tipo del documento: Article País de afiliación: Francia Pais de publicación: Estados Unidos

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