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Synthesis of glucosamine vinyl ether derivative and its deuterated analog

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Abstract

The use of calcium carbide (in the presence of H2O) as a source of acetylene in the reaction with methyl 2-amino-4,6-O-benzylidene-2-deoxy-β-d-glucopyranoside under superbasic conditions (KF, KOH, DMSO, 130 °C, 3 h) led to the corresponding vinyl ether in 78% yield. The vinylation does not affect other reaction centers. Replacement of water with deuterium oxide in the reaction mixture gave a stable deuterated analog of this vinyl ether in 72% yield. The one-step isotopic enrichment was practically quantitative (isotopic purity >96%). Introduced deuterium atoms can be used as a convenient label in further transformations.

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Authors and Affiliations

  1. St. Petersburg State University, 26 Universitetskii prosp., 198504, St. Petersburg, Russian Federation

    K. S. Rodygin, V. V. Voronin & M. S. Ledovskaya

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  1. K. S. Rodygin
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  2. V. V. Voronin
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  3. M. S. Ledovskaya
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Correspondence to K. S. Rodygin.

Additional information

Based on the materials of the XXI Mendeleev Congress on General and Applied Chemistry (September 9–13, 2019, St. Petersburg, Russia).

Published in Russian in Izyestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1401–1404, July, 2020.

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Rodygin, K.S., Voronin, V.V. & Ledovskaya, M.S. Synthesis of glucosamine vinyl ether derivative and its deuterated analog. Russ Chem Bull 69, 1401–1404 (2020). https://doi.org/10.1007/s11172-020-2915-3

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  • DOI: https://doi.org/10.1007/s11172-020-2915-3

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