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- W2007114600 abstract "Durch Einsatz der Tetraisopropyldisiloxyfunktion wird in einer fünfstufigen Synthese die Darstellung des selektiv geschützten 2,6-Di-O-methylmannopyranosids 5a erreicht. Außerdem läßt sich aus dem Galactopyranosid 7 in mehreren Schritten das α-Bromid der 4-O-Methylfucose 15 herstellen. Die Silbertriflatkondensation ergibt glatt das Disaccharid 16, ein Derivat der EF-Disaccharideinheit von Flambamycin. Zum Vergleich wurde aus 6a und 15 das Regioisomer 17 synthetisiert. Auf anderem Weg war das Fucosylbromid 25 zugänglich, das nach dem In-situ-Anomerisierungsverfahren mit 5a zum α,1→4-verknüpften Isomer 26 umgesetzt werden kann. Syntheses of Methyl 4-O-(β-D-Curacosyl)-α-D-curamicoside, the Glycoside of the Disaccharide Moiety EF of Flambamycin and Isomers By application of the tetraisopropyldisiloxy function a five-step synthesis of the selectively protected 2,6-di-O-methylmannopyranoside 5a is achieved. Additionally several steps are used to transfer the galactopyranoside 7 into the α-bromide of 4-O-methylfucose 15. By silver triflate-mediated condensation the disaccharide 16, a derivative of the disaccharide moiety EF of flambamycin, is obtained. For comparison, also 6a was glycosylated with 15 to yield the regioisomer 17. Another route made the fucosyl bromide 25 accessible. 25 could be condensed with 5a following the in-situ anomerization procedure to give the α,1→4-linked isomer 26." @default.
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- W2007114600 date "1987-04-27" @default.
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- W2007114600 title "Synthesen von Methyl-4-O-(β-D-curacosyl)-α-D-curamicosid, dem Glycosid der Disaccharideinheit EF von Flambamycin und Isomeren" @default.
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- W2007114600 doi "https://doi.org/10.1002/jlac.198719870324" @default.
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