BENZYL-FUNCTIONALIZED cycloSal-d4T MONOPHOSPHATES

J. Renze Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, Hamburg, D-20146, Germany

M. Plath Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, Hamburg, D-20146, Germany

C. Ducho Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, Hamburg, D-20146, Germany

J. Balzarini Rega Institute for Medical Research, Katholieke Universiteit, Minderbroeders-straat 10, Leuven, B-3000, Belgium

E. De Clercq Rega Institute for Medical Research, Katholieke Universiteit, Minderbroeders-straat 10, Leuven, B-3000, Belgium

C. Meier Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, Hamburg, D-20146, Germany

Abstract

Synthetic routes to benzyl-functionalized cycloSal-d4T monophosphates (7CH₂X-cycloSal-d4TMP) have been developed. Their hydrolytic behavior in basic aqueous solution (pH = 7.3) was studied and their hydrolysis half-lives were determined. It turned out that two different degradation pathways are leading to different products: beside the formation of the expected d4TMP and a styrene type derivative, a phenyl-d4T-phosphodiester was obtained as well. The product distribution was specified.

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BENZYL-FUNCTIONALIZED cycloSal-d4T MONOPHOSPHATES

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BENZYL-FUNCTIONALIZED cycloSal-d4T MONOPHOSPHATES

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