Simultaneous removal of benzyl and benzyloxycarbonyl protective groups in 5'-O-(2-deoxy-alpha-D-glucopyranosyl)uridine by catalytic transfer hydrogenolysis

Ilona Wandzik; Tadeusz Bieg; Monika Kadela

doi:10.1080/15257770802458303

Simultaneous removal of benzyl and benzyloxycarbonyl protective groups in 5'-O-(2-deoxy-alpha-D-glucopyranosyl)uridine by catalytic transfer hydrogenolysis

Nucleosides Nucleotides Nucleic Acids. 2008 Dec;27(12):1250-6. doi: 10.1080/15257770802458303.

Authors

Ilona Wandzik¹, Tadeusz Bieg, Monika Kadela

Affiliation

¹ Department of Organic Chemistry, Faculty of Chemistry, Silesian University of Technology, Gliwice, Poland. ilona.wandzik@polsl.pl

PMID: 19003570
DOI: 10.1080/15257770802458303

Abstract

Synthesis of N(3),2',3'-O-tris-(benzyloxycarbonyl)uridine and its use in the synthesis of 5'-O-(2-deoxy-alpha-d-glucopyranosyl)uridine is described. Simultaneous removal of benzyl and benzyloxycarbonyl groups was accomplished by catalytic transfer hydrogenolysis in the presence of Pearlman's catalyst without competing side reactions.

MeSH terms

Benzyl Compounds / chemistry*
Catalysis
Hydrogen / chemistry*
Hydrogenation
Molecular Structure
Uridine / chemistry*

Substances

Benzyl Compounds
Hydrogen
Uridine