Description
N2,9-Diacetylguanine is a purine compound that can be prepared by acetylation of guanine with acetic anhydride. It can be used in many fields such as organic synthesis, biological research and pharmaceutical manufacturing. N2,9-Diacetylguanine can be prepared into 2-amino-6-halogenated purine under the action of two-step PEG-2000 phase transfer catalyst and TPPB phase transfer catalyst, and further through the corresponding CuX-catalyzed diazotization reaction, new 2-halogenated purine compounds can be efficiently synthesized
[2]. In addition, it can also be used as an intermediate for the antiviral drugs Ganciclovir and Aciclovir.
Chemical Properties
white or brownish crystalline powder
Uses
N2,9-Diacetylguanine (Acicclovir EP Impurity L) is used to synthesize acyclic analogues of deoxyguanosine.
Application
The alkylation of N2,N9- diacetylguanine (DAG) with 2-oxa-1, 4-butane-dioldiacetate to give N2-acetyl-9-{2-acetoxyethoxymethyl}- guanine (N9 isomer) and/or N2-acetyl-7-{2-acetoxyethoxymethyl}- guanine (N7 isomer) in exceptionally high regioselectivity[1].
References
[1] Dharmendra Singh, Ashok Kumar, Mukesh J. Wani. “A Simple Solution to the Age Old Problem of Regioselective Functionalization of Guanine: First Practical Synthesis of Acyclic N9- and/or N7-Guanine Nucleosides Starting from N2,N9-Diacetylguanine.” The Journal of Organic Chemistry 64 13 (1999): 4665–4668.
[2] Y. HU. Synthesis of Some Biologically Active Halogenopurines[J]. Journal of the Korean Chemical Society-Daehan Hwahak Hoe Jee, 2010. DOI:10.5012/JKCS.2010.54.4.429.
