Synthesis of 4-oxo and 4-hydroxyimino-4-deoxy-Kdn2en derivatives

Article abstract of DOI:10.1080/07328309908544060

2,6-Anhydro-3-deoxy-D-manno-non-2-en-4-ulosonic acid (4-oxo-Kdn2en, 2) was synthesized from methyl 2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate (Kdn-2en methyl ester, 7) by the oxidation with manganese dioxide in dry acetone in good yield. 4-Hydroxyimino-Kdn2en derivatives (3), and 4-carbethoxymethylene-Kdn2en derivatives (4) were synthesized from the peracetylated methyl ester of 4-oxo-Kdn2en by oximation and Wittig reaction in good yield, respectively.

Full text of DOI:10.1080/07328309908544060

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Journal of Carbohydrate Chemistry
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Synthesis of 4-Oxo and 4-
Hydroxyimino-4-Deoxy-Kdn2En
Derivatives
Xue-Long Sun , Toshitsugu Kai , Noriko Sato , Hiroaki
Takayanagi & Kimio Furuhata
a
School of Pharmaceutical Sciences, Kitasato University ,
5
-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan
b
School of Pharmaceutical Sciences, Kitasato University ,
-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan
5
c
School of Pharmaceutical Sciences, Kitasato University ,
-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan
5
d
School of Pharmaceutical Sciences, Kitasato University ,
-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan
5
e
School of Pharmaceutical Sciences, Kitasato University ,
-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan
5
Published online: 27 Feb 2008.
To cite this article: Xue-Long Sun , Toshitsugu Kai , Noriko Sato , Hiroaki Takayanagi & Kimio
Furuhata (1999) Synthesis of 4-Oxo and 4-Hydroxyimino-4-Deoxy-Kdn2En Derivatives, Journal
of Carbohydrate Chemistry, 18:9, 1131-1138, DOI: 10.1080/07328309908544060
To link to this article: http://dx.doi.org/10.1080/07328309908544060
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