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- W2034336163 abstract "Abstract Reductive cleavage of the glycosidic carbon-oxygen bonds of methyl 2,3,4,6-tetra-O-methyl-β-d-glucopyranoside (1), methyl 2,3,4,6-tetra-O-methyl-α-d-glucopyranoside (2), permethylated cellulose (6) and permethylated cyclohexaamylose (7) was carried out in the presence of deuteriotriethylsilane, and the configuration of deuterium in the l-deuterio-1,5-anhydro-d-glucitol derivatives (4, 5 and 9, 10) that were produced was established by 1H- and 2H-NMR spectroscopy. All reductions were carried out with boron trifluoride etherate as the catalyst as originally reported [D. Rolf and G. R. Gray, J. Am. Chem. Soc., 104, 3539 (1982)], as well as with trimethylsilyl trifluoromethanesulfon-ate which we now report efficiently catalyzes the regiospecific reductive cleavage of glycosides. Spectroscopic studies revealed that the configuration of deuterium in the products was independent of the configuration of the starting glycoside. The predominant (∼95%) axial configuration observed leads us to propose that free oxonium ions (3 and 8) are formed as intermediates in these reductions." @default.
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- W2034336163 date "1983-01-01" @default.
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- W2034336163 title "Reductive Cleavage of Glycosides, Stereochemistry of Trapping of Cyclic Oxonium Ions" @default.
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- W2034336163 doi "https://doi.org/10.1080/07328308308057884" @default.
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