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- W2012940293 abstract "Umsetzung von Benzyl-β-D-arabinopyranosid (1) mit 1.5 aquivalenten Mesylchlorid lieferte ausschlieslich die 2,3-Di-O-mesyl-Verbindung 2. Behandlung mit Natriumazid in DMF ergab unter Inversion an C-2, C-3 und C-4 Benzyl-3,4-diazido-3,4-didesoxy-α-L-arabino-pyranosid (11). Saurekatalysierte Debenzylierung und anschliesende basenkatalysierte Umsetzung mit Trichloracetonitril fuhrte zum 1-O-aktivierten Trichloracetimidat 16, das mit dem 3,4-O-ungeschutzten 2-Azido-2-desoxyxylopyranosid 18 regiospezifisch das 3-O-ver-knupfte Disaccharid 20 lieferte. Reduktion der Azidgruppen, N-Acetylierung und O-Des-acetylierung fuhrte zum O-ungeschutzten Disaccharid 23. Die Strukturen der erhaltenen Verbindungen wurden, soweit erforderlich, uber O-acetylierte Derivate 1H-NMR-spektroskopisch gesichert.Glycosyl Imidates, 18.– Regioselective Reactions of Partially Protected Sugars Convenient Synthesis of 3,4-Diazido-3,4-dideoxy-L-arabinose from D-ArabinoseBenzyl β-D-arabinopyranoside (1) gave with 1.5 equivalents of mesyl chloride exclusively the 2,3-di-O-mesyl compound 2. Treatment with NaN3 in DMF caused inversion at C-2, C-3, and C-4 and yielded benzyl 3,4-diazido-3,4-dideoxy-α-L-arabinopyranoside (11). Acid-catalyzed debenzylation and subsequent base-catalyzed treatment with trichloroacetonitrile gave the 1-O-activated trichloroacetimidate 16; reaction with the 3,4-O-unprotected 2-azido-2-deoxyxylopyranoside 18 gave regiospecifically the 3-O-connected disaccaride 20. Reduction of the azido groups, N-acetylation, and O-deacetylation led to the O-unprotected disaccaride 23. the structures of the compounds obtained or their O-acetylated derivatives, respectively, were assigned by 1H NMR data." @default.
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- W2012940293 date "1985-08-12" @default.
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- W2012940293 title "Glycosylimidate, 18. Regioselektive Reaktionen partiell geschützter Zucker Einfache Synthese von 3,4-Diazido-3,4-didesoxy-L-arabinose aus D-Arabinose" @default.
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- W2012940293 doi "https://doi.org/10.1002/jlac.198519850804" @default.
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