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- W2147923894 abstract "2-Azido-2-desoxy-D-galactopyranose (1) läßt sich mit 1,3-Propandithiol in das offenkettige Dithioacetal 2 überführen, aus dem über 5 und 6 2-Azido-3,4,5-tri-O-benzoyl-2-desoxy-6-O-(methylsulfonyl)-D-galactose-trimethylendithioacetal (9) erhältlich ist. Dieses läßt sich mit Triphenylphosphan zum Piperidinderivat 10 cyclisieren. Hieraus ist nach Reduktion und Entblockierung 1,5-Didesoxy-1,5-imino-L-fucit (16) erhältlich. Die am Ringstickstoff von 16 gespacerten Verbindungen 13 und 18 wurden dargestellt. Monosaccharides Containing Nitrogen in the Ring, XXXVIII. – Synthesis of the α-L-Fucosidase Inhibitor 1,5-Dideoxy-1,5-imino-L-fucitol and of Some of Its Derivatives The reaction of 2-azido-2-deoxy-D-galactopyranose (1) with 1,3-propanedithiol yields the open-chained dithioacetal 2, which can be converted to 2-azido-3,4,5-tri-O-benzoyl-2-deoxy-6-O-(methylsulfonyl)-D-galactose trimethylene dithioacetal (9) via 5 and 6. Cyclization of 9 with triphenylphosphane results in the piperidine derivative 10. Reduction and debenzoylation of 10 leads to 1,5-dideoxy-1,5-imino-L-fucitol (16). Compounds 13 and 18 are synthesized, in which a spacer is linked to the nitrogen in the ring." @default.
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- W2147923894 date "1988-12-14" @default.
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- W2147923894 title "Monosaccharide mit Stickstoff im Ring, XXXVIII. Synthese des α-L-Fucosidase-Inhibitors 1,5-Didesoxy-1,5-imino-L-fucit und einiger seiner Derivate" @default.
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- W2147923894 doi "https://doi.org/10.1002/jlac.198819881203" @default.
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