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Periodate oxidation ofα-methyl-D-glucopyranoside, 6-0-trityl-α-methyl-D-glucopyranoside and 6-O-tritylcellulose in pyridine

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    A study was made of whether the periodate oxidation ofα-methyl-D-glucopyranoside, 6-O-trityl-α-methyl-D-glucopyranoside and 6-O-tritylcellulose can be run in dimethylformamide or pyridine.

  2. 2.

    The first step in the oxidation ofα-methyl-D-glucopyranoside by a solution of HIO4 in pyridine is a cleavage of the C3-C4 bond; the reaction of 6-O-trityl-α-methyl-D-glucopyranoside is less selective and is directed to a greater degree to the C2-C3 bond.

  3. 3.

    A method was developed for the homogeneous oxidation of 6-O-tritylcellulose with a solution of HIO4 in pyridine.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    R. G. Krylova, S. N. Ryadovskaya, L. I. Kostelian & A. I. Usov

Authors
  1. R. G. Krylova
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  2. S. N. Ryadovskaya
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  3. L. I. Kostelian
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  4. A. I. Usov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2068–2073, September, 1972.

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Krylova, R.G., Ryadovskaya, S.N., Kostelian, L.I. et al. Periodate oxidation ofα-methyl-D-glucopyranoside, 6-0-trityl-α-methyl-D-glucopyranoside and 6-O-tritylcellulose in pyridine. Russ Chem Bull 21, 2005–2009 (1972). https://doi.org/10.1007/BF00854627

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  • DOI: https://doi.org/10.1007/BF00854627

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