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- W2124185439 abstract "Für die Untersuchung der Stereochemie enzymatischer Protonierungsschritte bei Glucosylasen wurde Z)-3,7-Anhydro-1,2-didesoxy-D-gluco-oct-2-enitol (1) synthetisiert. Edukt für die mehrstufige Synthese ist die 3,4,5,7-Tetra-O-acetyl-2,6-anhydro-1-C-(1,3-diphenyl-2-imidazolidinyl)-D-glycero-D-gulo-heptose (4), die nach Kettenverlängerung durch Grignard-Reaktion die diastereomeren Alkohole 3,7-Anhydro-4,5,6,8-tetra-O-benzyl-1-desoxy-D-erythro-L-galacto-octitol (14) und -L-talo-octitol (15) liefert. Letztere werden nach O-Tosylierung der 2-Hydroxygruppe und Austausch der O-Benzylschutzgruppen gegen O-Acetylgruppen der Reaktion mit Natriumbenzoat unterworfen. 3,7-Anhydro-1-desoxy-4,5,6,8-tetra-O-acetyl-2-O-(p-tolylsulfonyl)-D-erythro-L-galacto-octitol (16) liefert neben dem Substitutionsprodukt 19 in nennenswerter Ausbeute 1. Zahlreiche Glucosylasen katalysieren die Umsetzung von 1 zu Additionsprodukten. Reactions of Enolic Sugar Derivatives, XVI. - Synthesis of a Diastereotopic Proton Probe [(Z-3,7-Anhydro-1,2-dideoxy-D-gluco-oct-2-enitol] for α- and β-D-Glucosylases For the elucidation of the stereochemistry in glucosylase-catalyzed proton addition reactions Z)-3,7-anhydro-1,2-dideoxy-D-gluco-oct-2-enitol (1) was synthesized. Starting material for the multistep synthesis is 3,4,5,7-tetra-O-acetyl-2,6-anhydro-1-C-(1,3-diphenyl-2-imidazolidinyl)-D-glycero-D-gulo-heptose (4), which after chain elongation by Grignard reaction yields the separable diastereomeric alcohols 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-desoxy-D-erythro-L-galacto-octitol (14) and -L-talo-octitol (15). After O tosylation of the hydroxy group in position 2 and replacement of the O benzyl by O acetyl groups in compounds 14 and 15, the resulting isomeric products were subjected to reaction with sodium benzoate. One isomer, 3,7-anhydro-1-deoxy-4,5,6,8-tetra-O-acetyl-2-O-(p-tolylsulfonyl)-D-erythro-L-galacto-octitol (16), yields the title compound 1 in reasonable quantity in addition to the nucleophilic substitution product 19. Several glucosylases catalyze the addition of water to the double bond of 1." @default.
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- W2124185439 date "1984-06-12" @default.
- W2124185439 modified "2023-10-16" @default.
- W2124185439 title "Reaktionen enolischer Zuckerderivate, XVI. Die Synthese einer diastereotopen Protonensonde [(Z)-3,7-Anhydro-1,2-didesoxy-D-gluco-oct-2-enitol] für α- und β-D-Glucosylasen" @default.
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- W2124185439 doi "https://doi.org/10.1002/jlac.198419840604" @default.
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