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Synthesis and allylic reactivity of α-bromomethyl β-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)oxy α,β-unsaturated carbonyl compounds

✍ Scribed by Ana Paula Esteves; Ana Maria Freitas; Clive M. Raynor; Richard J. Stoodley

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 260 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01842-5

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✦ Synopsis

Under radical conditions, N-bromosuccinimide converts a-methyl 1~-(2,3,4,6-tetra-O-acetyl-13-Dglucopyranosyl)oxy a,13-unsaturated carbonyl compounds into their c~-bromomethyl derivatives. The bromides undergo nucleophilic displacement reactions without rearrangement with azide, O-ethyl dithiocarbonate and thiocyanate anions; with acetate anion, there is a preference for the formation of rearranged acetates with reasonable stereoselection.

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