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- W2045144503 abstract "Durch oxidative Spaltung des D-Arabitderivats 3 wird das Dimere 5 der Benzyliden-D-threose erhalten. Die daraus durch saure Hydrolyse gewonnene D-Threose (11) liegt in Pyridinlosung vorwiegend als Gemisch der anomeren Furanosen 7 und 12 vor. Nach Darstellung des Trimethylendithioacetals 9 kann dessen selektive Isopropylidenierung entweder kinetisch zum endstandigen oder thermodynamisch zum mittelstandigen Dioxolanderivat 14 bzw. 16 gesteuert werden, Aus 16 wird uber mehrere Stufen 4-Desoxy-D-threose-trimethylendithioacetal (25) kristallin erhalten, dessen Metallierung zum Trianion nicht nachzuweisen war. Dagegen gelingt die Dimetallierung von 14, aus dem die diastereomeren Modellverbindungen 28 und 30 der Olivinseitenkette dargestellt werden konnten.Studies on D-Threose Derivatives and on the Preparation of the Olivin Side ChainOxidative cleavage of the D-arabinitol derivative 3 yields the dimer 5 of benzylidene D-threose. In pyridine solution D-threose (11), obtained by acid hydrolysis, predominantly represents a mixture of the anomeric furanoses 7 and 12. By either kinetic or thermodynamic isopropylidenation of the trimethylene dithioacetal 9 preparation of the terminal or the non-terminal dioxolane 14 or 16, respectively, is achieved selectively. Starting with 16 several steps lead to the crystalline 4-deoxy-D-threose trimethylene dithioacetal (25), by metallation of which the formation of a trianion could not be demonstrated. However, both the diastereomeric model compounds 28 and 30 of the olivin side chain were prepared via dimetallation of 14." @default.
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- W2045144503 date "1981-12-24" @default.
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- W2045144503 title "Untersuchungen über Derivate der D-Threose und zur Darstellung der Seitenkette von Olivin" @default.
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- W2045144503 doi "https://doi.org/10.1002/jlac.198119811210" @default.
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