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
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
Publication date: 2005-05-01