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- W2080116571 abstract "1,2-trans-2-Deoxy-2-iodoglycopyranosyl phosphoramidates (prepared from the corresponding glycals by addition of iodoazide, followed by Staudinger reaction with a phosphite) led by treatment with an alcohol in the presence of a base to the corresponding 1,2-trans-2-deoxy-2-phosphoramidoglycopyranosides, after inversion of configuration at C-1 and C-2. The reaction proceeded by an aziridine intermediate, which was opened by the alcohol present in the medium. Use of simple alcohols yielded alkyl glycosides having β-d-gluco, β-d-xylo, α-d-manno, and α-d-lyxo configurations, respectively, starting from α-d-manno, α-d-lyxo, β-d-gluco, and β-d-xylo phosphoramidates, with excellent yields. The same reaction with an alcohol derived from galactopyranose led to the expected disaccharide with a low yield. Les 1,2-trans-phosphoramidates de 2-désoxy-2-iodoglycosyles (préparés par addition de l'azoture d'iode sur les glycals, puis réaction de Staudinger avec un phosphite) traités par un alcool en présence d'une base conduisent aux 1,2-trans-2-désoxy-2-phosphoramidoglycopyranosides correspondants, après inversion de configuration au niveau de C-1 et C-2. La réaction procède par l'intermédiaire d'une aziridine en C-1–C-2, aussitôt ouverte par l'alcool présent dans le milieu. L'utilisation d'alcools simples ROH a permis la synthèse de glycosides d'alkyles de configuration β-d-gluco, β-d-xylo, α-d-manno et α-d-lyxo respectivement à partir des phosphoramidates α-d-manno, α-d-lyxo, β-d-gluco et β-d-xylo, avec d'excellents rendements. La même réaction appliquée à un alcool dérivé du galactopyranose, ne conduit à un disaccharide qu'avec un faible rendement." @default.
- W2080116571 created "2016-06-24" @default.
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- W2080116571 date "1988-04-01" @default.
- W2080116571 modified "2023-09-24" @default.
- W2080116571 title "Nouvelle voie d'accès aux 1,2-trans-2-amino-2-désoxyglycopyranosides par l'intermédiaire des phosphoramidates de 1,2-trans-2-désoxy-2-iodoglycopyranosyles" @default.
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- W2080116571 doi "https://doi.org/10.1016/0008-6215(88)80154-x" @default.
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