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Note | Regular issue | Vol 65, No. 8, 2005, pp.1967-1973
Published online, 27th May, 2005
DOI: 10.3987/COM-05-10430
A Practical Synthesis of 8-Hydroxyacyclovir and 9-(Carboxymethoxymethyl)guanine, Metabolites of Acyclovir

Teruo Kutsuma, Yasuo Sakai, Hiroyuki Ouchi, Noriaki Shiina, Takehiro Yamagishi, Shiroshi Shibuya, and Tsutomu Yokomatsu*

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

Improved methods for the synthesis of 8-hydroxyacyclovir and 9-(carboxymethoxymethyl)guanine, metabolites of acyclovir, were examined. The methods were found to be useful for practical preparation of 8-hydoxyacyclovir and 9-(caboxymethoxymethyl)guanine of high purity. Careful spectroscopic analysis of 8-hydroxyacyclovir in DMSO-d6 suggested that it may be exist in an 8-oxo tautomer rather than an 8-hydroxy tautomer under the solution conditions.