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- W2041128353 abstract "For oxidation in aqueous sodium metaperiodate at 20°, rate coefficients describing the decay of intact glycoside (kG) and the consumption of periodate (kP) were measured for the methyl α- and β-glycopyranosides of d-glucose, d-galactose. d-mannose, d-xylose, and d-(or l-)arabinose, and for methyl α-l-rhamnopyranoside. For glycosides containing a cis-1,2-diol group, kG was four to sixteen times larger than for those containing only trans-1,2-diol groups. For anomeric pairs, (kG)α/(kG)β varied from 0.6 to 1.7. The kinetics showed that the singly oxidised intermediates existed partly in an unreactive form, which was inferred to be a cyclic hemiacetal. For hexopyranosides, but not pentopyranosides, the stabilities of the hemiacetals, as indicated by the limiting values of kP, were much greater with α than with β anomers. From a consideration of possible structures and conformations of the hemiacetals, it was inferred that this result was a manifestation of the anomeric effect." @default.
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- W2041128353 date "1981-02-01" @default.
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- W2041128353 title "Periodate oxidation of methyl glycopyranosides: rate coefficients and relative stabilities of intermediate hemiacetals" @default.
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- W2041128353 doi "https://doi.org/10.1016/s0008-6215(00)85230-1" @default.
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