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• W2079842376 endingPage "1947" @default.
• W2079842376 startingPage "1939" @default.
• W2079842376 abstract "Generation of the molecular electrostatic potential (MEP) profiles, in color-coded form, on the solvent-accessible contact surfaces of the two main conformations that sucrose adopts in vacuo as well as in aprotic solvents (e.g. DMF), clearly shows the secondary glucosyl-2-OH to be the most electropositive of the altogether eight hydroxyl groups–conceivably due to the persistence of an intramolecular hydrogen bond of the 2g-O…︁HO-1f type. The notion that the 2g-OH is accordingly the hydroxyl group most readily deprotonated in aprotic solvents, and that the resulting sucrose 2g-O-alkoxide is the one best stabilized by intramolecular hydrogen bonding, received ample substantiation by smoothly achieving a highly regioselective (>80%) 2g-O-benzylation in DMF with NaH/benzyl bromide. The resulting 2g-O-benzyl-sucrose (2)– minor products being the 1f-O- (3) and 3f-O-isomers (4)– was converted, by acetylation and hydrogenolysis into the 2g-OH-free sucrose heptaacetate 6, isolable in crystalline form in 42% yield based on sucrose, thus opening up a ready entry to 2g-O-modified derivatives: 2-deoxy-sucrose (12) via radical deoxygenation of a 2g-O-thiocarbamate, 2-keto-sucrose perbenzoate 7 via PDC oxidation, or N-acetyl-sucrosamine 14 and its manno-analog 16 through oximation of 7 and subsequent borane reduction." @default.
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• W2079842376 date "1995-11-01" @default.
• W2079842376 modified "2023-10-09" @default.
• W2079842376 title "Molecular modeling of saccharides, 8. Selective 2-O-benzylation of sucrose: A facile entry to its 2-deoxy- and 2-keto-derivatives and to sucrosamine" @default.
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• W2079842376 doi "https://doi.org/10.1002/jlac.1995199511273" @default.
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