Ding Yongxian
2015
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Journal
Journal of Nanchang University
Abstract
9-[(2,3-Dihydroxypropoxy)methyl]guanine is one of the substances related to the antiviral drug ganciclovir as recorded in European Pharmcopoeia(Edition 8.0).A feasible synthetic protocol for the synthesis of 9-[(2,3-Dihydroxypropoxy)methyl]guanine was established in the current study.Using allylic alcohol as the starting material,the side chain 2,3-diacetoxy-1-acetoxymethyoxypropane was first prepared through chloromethylation of the hydroxyl group,substitution with potassium acetate,dihydroxylation of olefin and esterification with acetic anhydride.Then,the condensation of 2,3-diacetoxy-1-acetoxymethoxypropane with N2,9-diacetylguanine was catalyzed by p-toluenesulfonic acid monohydrate in N,N-dimethylformamide.The reaction was subsequently followed by hydrolysis with aqueous sodium hydroxide solution to produce the target molecule 9-[(2,3-Dihydroxypropoxy)methyl]guanine.Therefore,the new protocol could be used as reference in the quality control of ganciclovir.