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New Stereoselective Beta-Glycosylation via a Vinyl Oxirane Derived From D-glucal

Valeria Di Bussolo, Micaela Caselli, Mauro Pineschi, Paolo Crotti

Org Lett. 2002 Oct 17;4(21):3695-8.

PMID: 12375921

Abstract:

[reaction: see text] The reaction of the vinyl oxirane 1 derived from D-glucal with a series of O-nucleophiles (alcohols, phenol, and diacetone D-glucose) affords the corresponding 2-unsaturated beta-O-glycosides in a completely stereoselective way (syn 1,4-addition pathway). Epoxide 1 is generated in situ by treatment of the corresponding hydroxy mesylate 2 with t-BuOK in anhydrous benzene.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP299285 Calcium gluconate anhydrous Calcium gluconate anhydrous 299-28-5 Price
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