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Noncatalytic selective 6-O-acetylation of methyl 2,3-di-O-benzoyl-α-d-glucopyranoside with acetic acid and acetic anhydride

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Abstract

Noncatalytic acetylation of methyl 2,3-di-O-benzoyl-α-d-glucopyranoside with acetic acid or acetic anhydride proceeds regioselectively at the primary hydroxyl group and affords methyl 6-O-acetyl-2,3-di-O-benzoyl-α-d-glucopyranoside in good yield. The possibility of 6-O-acetylation should be taken into account when removing a 4,6-O-benzylidene protecting group with aqueous acetic acid at elevated temperature.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    Y. E. Tsvetkov, M. L. Gening & N. E. Nifantiev

Authors
  1. Y. E. Tsvetkov
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  2. M. L. Gening
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  3. N. E. Nifantiev
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Corresponding author

Correspondence to N. E. Nifantiev.

Additional information

This work was financially supported by the Russian Science Foundation (Project No. 19-43-02023).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2228—2230, November, 2020.

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Tsvetkov, Y.E., Gening, M.L. & Nifantiev, N.E. Noncatalytic selective 6-O-acetylation of methyl 2,3-di-O-benzoyl-α-d-glucopyranoside with acetic acid and acetic anhydride. Russ Chem Bull 69, 2228–2230 (2020). https://doi.org/10.1007/s11172-020-3026-x

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  • DOI: https://doi.org/10.1007/s11172-020-3026-x

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