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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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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 249-258 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Building Units of Oligosaccharides, LXXVIII. - Synthesis of KDO-Containing Lipid A AnaloguesThe non-neighbouring group supported glycosidation of 12 with the suitably protected glycosyl bromide 9 of 2-azido-2-deoxy-D-glucose leads - in the presence of a heterogeneous silver catalyst - to the formation of the β-(1→6)-glycosidically linked disaccharide 14. It consists of two 2-azido-2-deoxy-D-glucose units. Partial deblocking of 14 furnishes 15. On glycosidation with KDO bromide this compound yields the trisaccharide 16, which contains a KDO unit in an α-(2→6) ketosidic bond. Reduction of the two azido groups followed by amidation with (R)-3-hydroxymyristic acid and further deblocking generates the trisaccharide α-KDO-(2→6)-β-D-GlcA-(1→6)-D-GlcA 20 with two 3-hydroxy fatty acid residues in an amidic linkage.
    Notes: Die Umsetzung des Pyranosylbromids 9 der 2-Azido-2-desoxy-D-glucose mit dem Akzeptor 12 führt bei Gegenwart eines heterogenen Silberkatalysators ohne Nachbargruppenbeteiligung unter Inversion zum β-(1→6)-glycosidisch verknüpften Disaccharid 14 aus zwei 2-Azido-2-desoxy-D-glucose-Einheiten. Nach partieller Entblockierung zu 15 ist die Anknüpfung eines KDO-Restes unter Bildung einer α-(2→6)-ketosidischen Bindung zum Trisaccharid 16 möglich. Nach Reduktion der Azidogruppen und Anknüpfung von (R)-3-Hydroxymyristinsäure-Resten gelangt man nach Entblockierung zum Trisaccharid α-KDO-(2→6)-β-D-GlcA-(1→6)-D-GlcA 20, das amidartig zwei 3-Hydroxyfettsäure-Reste gebunden enthält.
    Type of Medium: Electronic Resource
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