An Alternative Approach to Isoganciclovir: A Prominent Impurity in the Antiviral Drug Ganciclovir

A simple and efficient process for the preparation of (±)-9-[(2,3-dihydroxypropoxy)methyl]guanine (isoganciclovir) is described. The synthesis features the preparation of a kinetically and thermodynamically controlled acyclic side chain using masked glycerol and methoxymethyl acetate. The unwanted r...

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Bibliographic Details
Published in:Scientia pharmaceutica 2015-04, Vol.83 (2), p.233-241
Main Authors: Sundaram, Dhanraj T S S, Kamat, Anand G, Prabahar, Koilpillai Joseph, Gupta, Peruri Badarinadh, Venkateswara Rao, Battula, Paul Douglas, Sanasi
Format: Article
Language:English
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Summary:A simple and efficient process for the preparation of (±)-9-[(2,3-dihydroxypropoxy)methyl]guanine (isoganciclovir) is described. The synthesis features the preparation of a kinetically and thermodynamically controlled acyclic side chain using masked glycerol and methoxymethyl acetate. The unwanted regioisomers were separated through selective crystallization, which upon deprotection yielded isoganciclovir in good yield. The present work explains the preparation of the acyclic side chain in a simple manner without the aid of any preparative column purification or separation technique.
ISSN:0036-8709
2218-0532
DOI:10.3797/scipharm.1409-15