Syntheses of 2,6-Anhydro-3-Deoxy-D-Glycero-D-Galacto-Non-2-Enonic Acid (Kdn2En) and Its Hydrogenation ProductsFootnote¹
1. Presented at the XVIIIth Znbmtional Carbohydrate Symposium, Milan, Italy, July 21-26, 1996.

Xue-Long Sun School of Pharmaceutical Sciences, Ktasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108, Japan

Toshitsugu Kai School of Pharmaceutical Sciences, Ktasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108, Japan

Hiroalu Takayanagi School of Pharmaceutical Sciences, Ktasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108, Japan

Kmio Furuhata School of Pharmaceutical Sciences, Ktasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108, Japan

Abstract

Methyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-glycero-D-galacto-enonate (5) was synthesized from KDN methyl ester 2 with a catalytic amount of concentrated sulfuric acid in acetic anhydride, or from 2-chloro-KDN methyl ester 4 with DBU in good yield. Hydrogenation of 4 and 5 with 10% Pd-C gave 2-deoxy-2-H_ax-KDN 8 and 2-deoxy-2-H_eq-KDN derivative 11 in high yield, respectively. The structures of these compounds were elucidated from the MS, elemental analysis, ¹H NMR and ¹³C NMR data.

1. Presented at the XVIIIth Znbmtional Carbohydrate Symposium, Milan, Italy, July 21-26, 1996.

Notes

1. Presented at the XVIIIth Znbmtional Carbohydrate Symposium, Milan, Italy, July 21-26, 1996.

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Syntheses of 2,6-Anhydro-3-Deoxy-D-Glycero-D-Galacto-Non-2-Enonic Acid (Kdn2En) and Its Hydrogenation ProductsFootnote¹
1. Presented at the XVIIIth Znbmtional Carbohydrate Symposium, Milan, Italy, July 21-26, 1996.

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Syntheses of 2,6-Anhydro-3-Deoxy-D-Glycero-D-Galacto-Non-2-Enonic Acid (Kdn2En) and Its Hydrogenation ProductsFootnote11. Presented at the XVIIIth Znbmtional Carbohydrate Symposium, Milan, Italy, July 21-26, 1996.

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Syntheses of 2,6-Anhydro-3-Deoxy-D-Glycero-D-Galacto-Non-2-Enonic Acid (Kdn2En) and Its Hydrogenation ProductsFootnote¹
1. Presented at the XVIIIth Znbmtional Carbohydrate Symposium, Milan, Italy, July 21-26, 1996.