An Allylic Rearrangement Arising from Reaction of Fluoride Ion and A 3-Chloro, 4,5-Unsaturated Uronate Derivative
Titel:
An Allylic Rearrangement Arising from Reaction of Fluoride Ion and A 3-Chloro, 4,5-Unsaturated Uronate Derivative
Auteur:
Kiss, Joseph Wyss, Pierre C. Flesch, Gerard Arnold, Wolf Noack, Klaus Schonholzer, Peter
Verschenen in:
Journal of carbohydrate chemistry
Paginering:
Jaargang 4 (1985) nr. 3 pagina's 347-361
Jaar:
1985-09-01
Inhoud:
Reaction of methyl [benzyl 2-[(benzyloxycarbonyl)-amino]-3-chloro-2,3,4-trideoxy-β-L-threo-hex-4-enopyrano-sid]uronate,3,4-trideoxy-β-L-threo-hex-4-enopyranosidjuronate (7) with silver fluoride gave the 5-fluoro, 3,4-unsaturated uronate derivative 8, which, on treatment with methanolic ammonia, afforded the corresponding 5-meth-oxy, uronamide 9. The structures of 8 and 9 were confirmed by spectral data and by x-ray crystallographic analysis of 8. 1H NMR spectroscopy parameters for 9 and its diastercomen 11 have been used to probe the conformational preferences in solution.