Synthesis of an Analog of Natural 3-Deoxyheptulosonic Acids on the Basis of Methyl 3-Chloro-3-deoxy-4,6:5,7-di-O-ethylidene-L-xylo-hept-2-ulosonate

Authors: Kornilov, V.; Glebova, Z.; Sudareva, T.

Source: Russian Journal of General Chemistry, Volume 75, Number 5, May 2005 , pp. 811-814(4)

Publisher: MAIK Nauka/Interperiodica

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Abstract:

The L-xylo analog of natural 3-deoxyheptulosonic acids can be synthesized by reductive dehalogenation of methyl 3-chloro-3-deoxy-4,6:5,7-di-O-ethylidene-L-xylo-hept-2-ulosonate. The direct oxidation with zinc dust involves the keto group and gives a mixture of epimeric 2-hydroxymethyl heptanoates which were characterized as acetates and oxidized with pyridinium dichromate into 3-deoxyheptulosonate. The indirect reduction involves formation, under the action of triphenylphosphine, of an enol phosphonium salt and its hydrolytic cleavage.

Document Type: Research article

DOI: http://dx.doi.org/10.1007/s11176-005-0323-x

Affiliations: 1: Institute of Physical and Organic Chemistry, Rostov State University, Rostov-on-Don, Russia,

Publication date: 2005-05-01