Catalytic Hydrogenation of Phosphate Enol Esters Present in Branched Chain Dienepyranosides in a Route to Thromboxane Analogs from D-Galactose

OSCAR MORADEI; CECILE M. DU MORTIER; ALICIA FERNÁNDEZ CIRELLI; JOACHIM THIEM

JOURNAL OF CARBOHYDRATE CHEMISTRY

Taylor & Francis

Año: 1999 vol. 18 p. 15 - 29

0732-8303

Abstract Branched-chain conjugated dienepyranosides including vinyl phosphate esters were subjected to catalytic hydrogenation under different conditions. Heterogeneous catalysts led to isomerization products that were resistant to further hydrogenation. On the other hand, under homogeneous conditions, complete stereoselective hydrogenation was achieved. Methyl 2,4-dideoxy-3-O-diethoxyphosphoryl-4-C-[(methoxycarbonyl)methyl]--D-ribo-hexopyranoside (6b), a potential precursor of thromboxane analogs, was obtained.