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- W2103157060 abstract "The O-benzylated α and β-glucosyl trichoroacetimidates 1a–α and 1a–β afforded with the phosphinic acid derivative 2 and the phosphonic acid derivative 3 directly the corresponding O-glucosylated products 4 and 5, resp., with inversion at the anomeric center. The corresponding O-acetylated trichloroacetimidates 1b–α and 1b–β provided both the β-products due to neighboring group participation. With the amidophosphoric acid derivative 6 and the trichloroacetimidate 1b–α the O-glucosylated compound 8–β was obtained. The O-acetylated 6-deoxy-L-talopyranosyl donor 12 behaved similarly. With compound 2 the α-phosphinate 13 was formed. Dibenzyl phosphate gave the α-phosphate 14; subsequent debenzylation led to the 6-deoxy-α-L-talopyranosyl phosphate 15. Glycosylimidate, 37. — Direkte O-Glycosylierung von Verbindungen mit PO(OH)-Gruppen Die O-benzylierten α- und β-Glucosyl-trichloracetimidate 1a–α und 1a–β reagierten mit dem Phosphinsäurederivat 2 bzw. mit dem Phosphonsäurederivat 3 unter Inversion der Konfiguration am anomeren Zentrum direkt zu den entsprechenden O-glucosylierten Produkten 4 bzw. 5. Die O-acetylierten Trichloracetimidate 1b–α und 1b–β lieferten beide infolge Nachbargruppenbeteiligung der 2-O-Acetylschutzgruppe die entsprechenden β-Produkte. Mit dem Phosphorsäureamid-Derivat 6 und dem Trichloracetimidat 1b–α wurde die O-glucosylierte Verbindung 8–β erhalten. Der O-acetylierte 6-Deoxy-L-talopyranosyl-Donor 12 zeigte ein analoges Verhalten. Mit Verbindung 2 wurde das α-Phosphinat 13 gebildet. Dibenzylphosphat lieferte das α-Phosphat 14, das durch Debenzylierung das 6-Desoxy-α-L-talopyranosylphosphat 15 ergab." @default.
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- W2103157060 date "1988-07-14" @default.
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- W2103157060 title "Glycosyl imidates, 37. DirectO-glycosylation of compounds containing a PO(OH) moiety" @default.
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- W2103157060 doi "https://doi.org/10.1002/jlac.198819880710" @default.
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