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Sci. Pharm. 2015, 83(2), 233-241; doi:10.3797/scipharm.1409-15

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

1
Chemical Research and Development, APL Research Centre-II, Aurobindo Pharma Ltd., Survey No. 71 & 72, Indrakaran (V), Medak District-502 329, Andhra Pradesh, India.
2
Department of Engineering Chemistry, Andhra University College of Engineering (A), Andhra University, Visakhapatnam-530003, Andhra Pradesh, India.
*
Author to whom correspondence should be addressed.
Received: 27 September 2014 / Accepted: 11 November 2014 / Published: 11 November 2014
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Abstract

A simple and efficient process for the preparation of (±)-9-[(2,3-dihydroxy-propoxy)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.
Keywords: Anti-herpes; Cytomegalovirus; Methoxymethyl acetate; Valganciclovir hydrochloride Anti-herpes; Cytomegalovirus; Methoxymethyl acetate; Valganciclovir hydrochloride
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

SUNDARAM, D.T.S.S.; KAMAT, A.G.; PRABAHAR, K.J.; GUPTA, P.B.; VENKATESWARA RAO, B.; PAUL DOUGLAS, S. An Alternative Approach to Isoganciclovir: A Prominent Impurity in the Antiviral Drug Ganciclovir. Sci. Pharm. 2015, 83, 233-241.

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