A New Synthesis of Acyclovir Prodrugs.N 2-Acetylacyclovir and 6-Deoxyacyclovir
- 1 January 1990
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1990 (06) , 461-464
- https://doi.org/10.1055/s-1990-26904
Abstract
9-(2-Acetoxyethoxy)-2-amino-1,9-dihydro-6H-purin-6-one (1b) and 2-acetylamino-9-(2-hydroxyethoxy)methyl-1,9-dihydro-6H-purin-6-one (N2-acetylacyclovir 3) were prepared from 9-[(2-acetoxyethoxy)methyl] -2-acetylamino-1,9-dihydro-6H-purin-6-one (1a) using regioselective deacetylation procedures. Compounds 1a and 1b were chlorinated with phosphoryl chloride to give 9-[(2-acetoxyethoxy)methyl]-2-acetylamino-6-chloro-9H-purine (4a) and its N2-deacetylated counterpart (4b), respectively. Subsequent reductive dechlorination of 4a and 4b under conditions of catalytic transfer hydrogenolysis followed by deprotection afforded 6-deoxy-acyclovir (7) in a good overall yield.Keywords
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