Direct epoxidation of d-glucal and d-galactal derivatives with in situ generated DMDO

Pavel Cheshev; Alberto Marra; Alessandro Dondoni

doi:10.1016/j.carres.2006.09.003

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Direct epoxidation of d-glucal and d-galactal derivatives with in situ generated DMDO

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Direct epoxidation of d-glucal and d-galactal derivatives with in situ generated DMDO

Pavel Cheshev, Alberto Marra et Alessandro Dondoni

Carbohydrate research, Vol.341(16), pp.2714-2716

27/11/2006

DOI: https://doi.org/10.1016/j.carres.2006.09.003

PMID: 17014831

Résumé

1,2-Anhydro- d-galactopyranose

1,2-Anhydro- d-glucopyranose

Dimethyldioxirane

DMDO

Epoxidation

A multi-gram epoxidation of 3,4,6-tri- O-benzyl- d-glucal and d-galactal with dimethyldioxirane (DMDO) generated in situ from Oxone ®/acetone in a biphasic system (CH 2Cl 2–aqueous NaHCO 3) resulted in the formation of the corresponding 1,2-anhydrosugars in a 99% yield and 100% selectivity. In a similar way, 3,4,6-tri- O-acetyl- d-glucal afforded a 7:1 mixture of the corresponding gluco and manno derivatives in an 87% overall yield.

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Détails

Titre: Direct epoxidation of d-glucal and d-galactal derivatives with in situ generated DMDO
Créateurs - sans rôle: Pavel Cheshev
Alberto Marra
Alessandro Dondoni
Détails de publication: Carbohydrate research, Vol.341(16), pp.2714-2716
Éditeur: Elsevier Ltd
Nombre de pages: 3
Identifiants: 99163337109311
Unité académique: Institut des Biomolécules Max Mousseron - IBMM
Langue: English
Type de ressource: Journal article