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Regio- and stereo-selective bromoalkoxylations of (E)-α-(2′,3′,4′,6′,-tetra-O-acetyl-β-d-glucopyranosyloxymethylene) carbonyl compounds: a route to stereopure α-bromo-α-dioxymethyl carbonyl compounds

✍ Scribed by M.Sum Idris; David S. Larsen; Anthony Schofield; Richard J. Stoodley; Peter D. Tiffin


Publisher
Elsevier Science
Year
1995
Tongue
French
Weight
228 KB
Volume
36
Category
Article
ISSN
0040-4039

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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 dithiocarbona