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  • 1
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Branched and Chain-extended Sugars, XXX.  -  Diastereoselective Synthesis of L-glycero-D-manno-Heptose, a Constituent of the Inner Core Region of LipopolysaccharidesReaction of 2,3;5,6-di-O-isopropylidene-D-mannofuranose (1) with 2-lithio-1,3-dithiane affords diastereoselectively the 3,4;6,7-di-O-isopropylidene-D-glycero-D-galacto-heptose trimethylene dithioacetal (3). Conversion of compound 3 by a sequence of steps gives the tri-O-isopropylidene-D-glycero-D-galacto-heptit 16 which is oxidized with 1,1′-(azodicarbonyl)-dipiperidine to give the tri-O-isopropylidene-L-glycero-D-manno-heptose 17. Finally, compound 17 is transferred via the acetate 19 into the L-glycero-D-manno-heptopyranose 18.
    Notes: 2,3;5,6-Di-O-isopropyliden-D-mannofuranose (1) reagiert diastereoselektiv mit 2-Lithio-1,3-dithian zum 3,4;6,7-Di-O-isopropyliden-D-glycero-D-galacto-heptose-trimethylendithioacetal (3). Nach Umwandlung von 3 über eine Reihe von Zwischenstufen zum Tri-O-isopropyliden-D-glycero-D-galacto-heptit 16 läßt sich dieser mit 1,1′-(Azodicarbonyl)dipiperidin zur Tri-O-isopropyliden-L-glycero-D-manno-heptose 17 oxidieren. Hieraus ist über das Acetat 19 die freie L-glycero-D-manno-heptopyranose 18 zu gewinnen.
    Type of Medium: Electronic Resource
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