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Chloroglycidate Synthesis of a Precursor of Natural 3-Deoxy-D-manno-octulosonic Acid with Combined Protective Groups

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Abstract

A new oxo form of D-mannose with cyclohexylidene and benzyl protective groups is synthesized with the aim of adapting the chloroglycidate synthesis for natural 3-deoxy-D-manno-octulosonic acid. The sites of fixation of the protective groups were established by converting a model compound, 4-O-acetyl-2,3: 5,6-di-O-cyclohexylidene-aldehydo-D-mannose, into a known dicyclohexylidene-D-manno-furanose. The oxo form was reacted with methyl dichloroacetate to obtain a stereoisomeric mixture of chloroglycidates which were transformed into the corresponding pyruvate. The ketone and enol forms of the latter compound were isolated and separately characterized.

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Authors and Affiliations

  1. Research Institute of Physical and Organic Chemistry, Rostov State University, Rostov-on-Don, Russia

    V. I. Kornilov, Z. I. Glebova, S. V. Turik, I. I. Bicherova & Yu. A. Zhdanov

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  1. V. I. Kornilov
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  2. Z. I. Glebova
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  3. S. V. Turik
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  4. I. I. Bicherova
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  5. Yu. A. Zhdanov
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Kornilov, V.I., Glebova, Z.I., Turik, S.V. et al. Chloroglycidate Synthesis of a Precursor of Natural 3-Deoxy-D-manno-octulosonic Acid with Combined Protective Groups. Russian Journal of General Chemistry 74, 225–229 (2004). https://doi.org/10.1023/B:RUGC.0000025507.24993.c6

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  • DOI: https://doi.org/10.1023/B:RUGC.0000025507.24993.c6

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