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- W2013850217 abstract "Kondensation des Modell-Iridoidaglycons 2a mit 2,3,4,6-Tetraacetyl-α-D-glucosylbromid (5a) und Silberperchlorat sowie mit 2,3,4,6-Tetraacetyl-β-D-glucose (5b) und Bortrifluorid/Ether lieferte nach Solvolyse mit Bariumhydroxid in Methanol die Dimeren 18a–j und die isomeren Glucoside 13b, 13e und 14b. Bei der Reaktion mit 5a erhielt man zusätzlich die an C-2′ verknüpften Glucose-Derivate 15a/b. Die Glucosidierung der Aglycon-silylether 6a/b und -bromide 6c/d wurde ebenfalls untersucht. Umsetzung von 6-O-Acetylloganinaglycon (3) mit 5a und Silberperchlorat ergab nach Solvolyse zu 13% das β-Glucosid Loganin (1) und zu 5.4% das α-Glucosid 21b. Dieses Verfahren weist gegenüber der Kondensation von 3 mit 5b und Bortrifluorid/Ether eine höhere Stereoselektivität auf. Iridoids, IX: Investigation towards the Synthesis of Iridoidglucosides Condensation of the model-iridoidaglycon 2a with 2,3,4,6-tetraacetyl-α-D-glucosyl bromide (5a) and silver perchlorate as well as 2,3,4,6-tetraacetyl-β-D-glucose (5b) and boron trifluoride/ether yielded after solvolysis with barium hydroxide in methanol the dimers 18a–j and the isomeric glucosides 13b, 13e and 14b. In addition the C-2′ connected glucose derivatives 15a/b were formed in the reaction of 2a with 5a. Furthermore the glucosidation of the aglycon-silylethers 6a/b and -bromides 6c/d was investigated. — Treatment of the 6-O-acetylloganinaglycon 3 with 5a and silver perchlorate led after solvolysis with 13% yield to the β-glucoside loganin (1) and with 5.4% yield to the α-glucoside 21b. This method has a higher stereoselectivity than the condensation of 3 with 5b and boron trifluoride/ether." @default.
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- W2013850217 date "1978-06-01" @default.
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- W2013850217 title "Iridoide, IX: Untersuchungen zur Synthese von Iridoidglucosiden" @default.
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- W2013850217 doi "https://doi.org/10.1002/cber.19781110637" @default.
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