An Allylic Rearrangement Arising from Reaction of Fluoride Ion and A 3-Chloro, 4,5-Unsaturated Uronate Derivative |
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| Authors: | Joseph Kiss Pierre C Wyss Gerard Flesch Wolf Arnold Klaus Noack Peter Schönholzer |
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| Institution: | 1. Pharmaceutical Research Department , Central Research Units F. Hoffmann-La Roche &2. Co., Ltd. , Basle, Switzerland;3. Co., Ltd. , Basle, Switzerland;4. Ecole Nationals Supérieure de Chimie de Mulhouse , Mulhouse, France |
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| Abstract: | 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. |
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