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- W2028012938 abstract "Oxidation of 4-cyanophenyl 2,5-anhydro-1,6-dithio-α-d-glucoseptanoside with magnesium monoperoxyphthalate (MMPP) resulted in a mixture containing two endo- and two exo-monosulfoxides as well as two endo-exo bis-sulfoxides differing in the chirality of the sulfoxide groups. Besides the aforementioned six products a further endo–exo bis-sulfoxide isomer as well as an exo-sulfone was obtained via oxidation with NaIO4. Oxidation of 4-nitrophenyl 1,5-dithio-β-d-arabinopyranoside with MMPP yielded only two endo-sulfoxides, while oxidation with NaIO4 in turn led to cleavage of the carbohydrate ring. The formed dialdehyde was stabilized by cyclisation to a hemiacetal, which on further treatment with MMPP afforded an exo-monosulfoxide. The position of oxidation as well as the chirality of the respective sulfoxide groups was established by NMR spectroscopy and X-ray crystallography." @default.
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- W2028012938 date "2002-01-01" @default.
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- W2028012938 title "The behavior of two thiosugar thioglycosides towards oxidation" @default.
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- W2028012938 doi "https://doi.org/10.1016/s0957-4166(02)00034-4" @default.
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