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- W2055819791 abstract "Bei der Wolff-Umlagerung von 1-Diazo-1-desoxy-3.4.5.6.7-penta-O-acetyl-D-glucoheptulose (7) entsteht nicht 2-Desoxy-3.4.6.7-tetra-O-acetyl-D-glucoheptonsäure-lacton-(1.5) (8), sondern 4.5.6.7-Tetra-acetoxy-D-arabo-hepten-(2)-säure (9). Entsprechend liefert 1.8-Bisdiazo-1.8-bisdesoxy-3.4.5.6-tetra-O-acetyl-galakto-octodiulose (1) die meso-4.5-Diacetoxy-octadien-(2.6)-disäure (3). Während die katalytische Hydrierung von 9 unter Bildung der 2.3-Bisdesoxy-4.5.6.7-tetra-O-acetyl-D-arabo-heptonsäure (11) verläuft, wird aus der Dicarbonsäure 3 Octandisäure (6) erhalten. Longer-chain Carbohydrate Derivatives with Reactive Endgroups, IV1). Formation of a,ß-Unsaturated Carboxylic Acid Derivatives by Wolff Rearrangement of the Diazoketones from 2,3,4,5,6-Penta-O-acetyl-D-gluconyl Chloride and 2,3,4,5-Tetra-O-acetyl-galactaroyl Dichloride The Wolff rearrangement of 1-diazo-1-deoxy-3,4,5,6,7-penta-O-acetyl-D-glucoheptulose (7) does not yield 2-deoxy-3,4,6,7-tetra-O-acetyl-D-glucoheptonolactone-(1,5) (8) but 4,5,6,7-tetra-O-acetyl-D-arabo-hept-2-enoic acid (9). In accordance with this result, 1,8-bisdiazo-1,8-dideoxy-3,4,5,6-tetra-O-acetyl-galacto-octodiulose (1) yields meso-4,5-di-O-acetyl-octa-2,6-dienic acid (3). While teh catalytic hydrogenation of 9 proceeds with the formation of 2,3-dideoxy-4j,5,6,7-tetra-O-acetyl-D-arabo-heptonic acid (11), the dicarboxylic acid 3 forms octanedioic acid (6)." @default.
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- W2055819791 date "1970-01-01" @default.
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- W2055819791 title "Längerkettige Kohlenhydrat-Derivate mit reaktiven Endgruppen, IV1) Bildung α.β-ungesättigter Carbonsäure-Derivate durch Wolff-Umlagerung der Diazoketone aus 2.3.4.5.6-Penta-O-acetyl-D-gluconsäure-chlorid und 2.3.4.5-Tetra-O-acetyl-galaktarsäure-dichlorid" @default.
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- W2055819791 doi "https://doi.org/10.1002/jlac.19707350118" @default.
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