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The synthesis ofN-acetyl-β-l-fucosamine-1-phosphate and uridine 5′-diphospho-N-acetyl-β-l-fucosamine

  • Chemistry of Natural Compounds and Bioorganic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

Uridine 5′-(2-acetamido-2,6-dideoxy-β-l-galactopyranosyl) diphosphate (uridine 5′-diphospho-N-acetyl-β-l-fucosamine) was synthesized. The key intermediate, 3,4-di-O-acetyl-2-azido-2,6-dideoxy-β-l-galactopyranosyl dibenzyl phosphate, was prepared by a previously unknown reaction of cesium dibenzyl phosphate with the corresponding α-glycosyl nitrate and was then converted into theN-acetylated glycosyl phosphate and nucleoside diphosphate sugarsvia 3,4-di-O-acetyl-2-amino-2,6-dideoxy-β-l-galactopyranosyl phosphate using mildN-acetylation andO-deacetylation as the last synthetic steps.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation

    P. A. Illarionov, V. I. Torgov & V. N. Shibaev

  2. Medical School, University of Newcastle, Framlington Place, NE2 4HH, Newcastle upon Tyne, UK

    I. Hancock

Authors
  1. P. A. Illarionov
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  2. V. I. Torgov
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  3. I. Hancock
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  4. V. N. Shibaev
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Published inIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 11, pp. 1919–1923, November, 2000.

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Illarionov, P.A., Torgov, V.I., Hancock, I. et al. The synthesis ofN-acetyl-β-l-fucosamine-1-phosphate and uridine 5′-diphospho-N-acetyl-β-l-fucosamine. Russ Chem Bull 49, 1891–1894 (2000). https://doi.org/10.1007/BF02494930

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  • DOI: https://doi.org/10.1007/BF02494930

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