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- W1978490910 abstract "Mit dem Lactose-Derivat 4 mit unsubstituierten 3′OH und 4′OHGruppen ist eine regioselektive Glycosylierung je nach Wahl des Katalysator-Systems möglich. Mit dem Phthalimidobromid 1 reagiert 4 in homogener Phase bei Gegenwart von Silbertriflat regioselektive zum β(1→3)-glycosidisch verknüpften Trisaccharid 5. Die gleichen Verbindungen reagieren dagegen in heterogener Phase mit Silbersilicat regioselektive zum β (1→4)-glycosidisch verknüpften Trisaccharid 7. Umsetzung von 4 mit dem Azido-Halogenid 2 ergibt bei Gegenwart von Silbersilicat in heterogener Phase ebenfalls regioselektive das β(1→4)-glycosidisch verknüpfte Produkt 17. In homogener Phase bei Gegenwart von Silberperchlorat liefern dagegen die Azido-Halogenide 2 und 3 nach dem in-situ-Anomerisierungsverfahren α-glycosidisch verknüpfte Produkte. Building Units of Oligosaccharides, LVIII. — Regioselective Glycosylation at 3′OH or 4′OH of Lactose Using Different Catalyst Systems The lactose derivative 4 with unsubstituted 3′OH and 4′OH groups makes regioselective glycosylation reactions possible depending on the chosen type of catalyst system. In the presence of silver triflate, 4 reacts in homogenic phase with the phthalimido bromide 1 to yield the β(1→3)-glycosidically linked trisaccharide 5. The same compounds give in heterogenic phase with silver silicate regioselectively the β(1→4)-glycosidically linked trisaccharide 7. In the presence of silver silicate, 4 reacts with the azido halide 2 to yield in heterogenic phase regioselectively the β(1→4)-glycosidically linked product 17. In homogenic phase with silver perchlorate, however, the azido halides 2 and 3 yield the α-glycosidically linked products, following the in situ anomerization procedure." @default.
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- W1978490910 date "1985-01-14" @default.
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- W1978490910 title "Bausteine von Oligosacchariden, LVIII. Regioselektive Glycosylierung an 3′-OH oder 4′-OH der Lactose durch Einsatz unterschiedlicher Katalysator-Systeme" @default.
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- W1978490910 doi "https://doi.org/10.1002/jlac.198519850114" @default.
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