First O-glycosylation of hydroxamic acids.
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.
Thomas
Mickaël
M
UMR 6514, Synthèse et Réactivité des Substances Naturelles, Université de Poitiers et CNRS, 40, Av. du Recteur Pineau, 86022 Poitiers, France.
Gesson
Jean-Pierre
JP
Papot
Sébastien
S
D000081:Acetamides; D002236:Carbohydrate Conformation; D005463:Fluoroacetates; D006031:Glycosylation; D006877:Hydroxamic Acids / Q000737:chemistry*; D015394:Molecular Structure; D014269:Trifluoroacetic Acid / Q000737:chemistry
D000081:Acetamides; D005463:Fluoroacetates; D006877:Hydroxamic Acids; C030688:trifluoroacetamide; D014269:Trifluoroacetic Acid