EventsThe 3rd International Electronic Conference on Synthetic Organic Chemistry
Published
This submission belongs to the session a. General Organic Synthesis of the event The 3rd International Electronic Conference on Synthetic Organic Chemistry
Published date
01 Nov, 1999
Citation
Ramachandra S. Hosmane, Zhiyuan Sun, A New, Improved Synthesis of 9-Benzyladenine: An Important Heterocyclic Analogue of Adenosine Useful for Chemical and Biochemical Research of Nucleic Acids, in Proceedings of The 3rd International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 1999, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-3-01746
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A New, Improved Synthesis of 9-Benzyladenine: An Important Heterocyclic Analogue of Adenosine Useful for Chemical and Biochemical Research of Nucleic Acids

Zhiyuan Sun 1
1. Research Institute of Elemento Organic Chemistry, Nankai University 94 Weijin Road, Tianjin 300071, Peoples Republic of China
2. Laboratory for Drug Design and Synthesis, Department of Chemistry & Biochemistry University of Maryland, Baltimore County (UMBC), 1000 Hilltop Circle Baltimore, Maryland 21250, USA
Abstract
9-Benzyladenine (I) is a rare chemical often used by chemists, biochemists, as well as biophysical chemists doing research in the field of nucleic acids as a convenient heterocyclic base model for physicochemical comparison with adenosine. However, I is commercially unavailable, and the synthetic methods available from the literature are tedious and poor yielding. We have synthesized I from 5-amino-1-benzyl-4-cyanoimidazole (II) which, in turn, was synthesized from acyclic precursors, III, IV or V, using three different methods. We report herein all these methods, along with our recommendation for the best method in terms of both convenience and product yield to access both the imidazole precursor II and the target 9-benzyladenine (I).
Keywords
Improved Syntheses of 9-Benzyladenine and 5-Amino-4-cyano-1-benzylimidazole
Synthesis of Novel Acyclic Nucleoside and Acyclic Nucleoside Phosphonate Analogues of a Ring-Expanded ("Fat") Nucleobase Containing the Imidazo[4,5-e][1,3]diazepine Ring System.
Titanocenes Catalyzed Diastereoselective Epoxidation of Allylic Alcohols.