Studies on sialic acids. XV. Synthesis of .ALPHA.- and .BETA.-O-glycosides of 3-deoxy-D-glycero-D-galacto-2-nonulopyranosonic acid(KDN).

NAKAMURA MITSUNOBU, FURUHATA KIMIO, OGURA HARUO

doi:10.1248/cpb.36.4807

Studies on sialic acids. XV. Synthesis of .ALPHA.- and .BETA.-O-glycosides of 3-deoxy-D-glycero-D-galacto-2-nonulopyranosonic acid(KDN).

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NAKAMURA MITSUNOBU

School of Pharmaceutical Sciences, Kitasato University
FURUHATA KIMIO

School of Pharmaceutical Sciences, Kitasato University
OGURA HARUO

School of Pharmaceutical Sciences, Kitasato University

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説明

3-Deoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (KDN) was synthesized by basecatalyzed condensation in good yield. Furthermore, benzyl (methyl 3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosid) onate and sodium 2-(5-cholesten-3β-yloxy)-3-deoxy-D-eycero-α-and β-D-galacto-2-nonulopyranosonate were synthesized under Koenigs-Knorr-like reaction conditions, using benzyl (4, 5, 7, 8, 9-penta-O-acety1-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosyl bromid)-onate as a glycosyl donor. The structure and the stereochemistry of glycosylation products were determined by proton nuclear magnetic resonance and circular dichroism spectral analysis.