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Nucleosides and Nucleotides Volume 11, 1992 - Issue 6
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Original Articles

N2-Isobutyryl-O6-[2-(p-Nitrophenyl)Ethyl]Guanine: A New Building Block for the Efficient Synthesis of Carbocyclic Guanosine Analogs

Thomas F. Jenny Laboratory for Organic Chemistry, E.T.H., CH-8092, Zürich, Switzerland; Department of Chemistry, M.I.T., Cambridge, MA, 02139, USA
,
K. Christian Schneider Laboratory for Organic Chemistry, E.T.H., CH-8092, Zürich, Switzerland; Biotechnologie Gründungsgesellschaft, Theodor-Heuss-Ring 42, D-5000, Koeln 1, Germany
&
Steven A. Benner Laboratory for Organic Chemistry, E.T.H., CH-8092, Zürich, Switzerland
Pages 1257-1261 | Received 25 Nov 1991, Accepted 17 Dec 1991, Published online: 23 Sep 2006

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Dhrubajyoti Datta. (2020) A convenient route to synthesize N2-(isobutyryl)-9-(carboxymethyl)guanine for aeg-PNA backbone. Nucleosides, Nucleotides & Nucleic Acids 39:4, pages 530-541.
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VincentD. Antle & CarolA. Caperelli. (1999) Synthesis of Chiral Carbocyclic Ribonucleotides. Nucleosides and Nucleotides 18:9, pages 1911-1928.
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Jinglan Zhou, Jui-Yi Tsai, Kamal Bouhadir & PhilipB. Shevlin. (1999) N2-Acetyl-O6-(2-(P-Nitrophenyl)Ethyl)Guanine: A Convenient Building Block for the Synthesis of 9-Substituted Guanine Derivatives. Synthetic Communications 29:17, pages 3003-3009.
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L. Kovács, Z. Timár & B. Penke. (1999) Synthesis of Peptide Nucleic Acid Monomers. Nucleosides and Nucleotides 18:4-5, pages 727-729.
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Laurent Schmitt & CarolA. Caperelli. (1997) Synthesis of the Optically Active Carbocyclic Analogs of the Four 2′-Deoxyribonucleoside Monophosphates. Nucleosides and Nucleotides 16:12, pages 2165-2192.
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DanielC. Capaldi, Alessandra Eleuteri, Qin Chen & RaymondF. Schinazi. (1997) Synthesis of Six-Membered Nucleoside Analogs. Part 1: Pyrimidine Nucleosides Based on the 1,3-Dioxane Ring System. Nucleosides and Nucleotides 16:4, pages 403-416.
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DavidL. Hughes. (1996) PROGRESS IN THE MITSUNOBU REACTION. A REVIEW. Organic Preparations and Procedures International 28:2, pages 127-164.
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Alexei A. Koshkin, Jef Fensholdt, Henrik M. Pfundheller & Christian Lomholt. (2001) A Simplified and Efficient Route to 2‘- O , 4‘- C -Methylene-Linked Bicyclic Ribonucleosides (Locked Nucleic Acid) . The Journal of Organic Chemistry 66:25, pages 8504-8512.
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Ian D. Jenkins & Oyo Mitsunobu. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Yun Wu, Jie-Cheng Xu, Jing Liu & You-Xing Jin. (2001) Synthesis of N -Boc and N -Fmoc dipeptoids with nucleobase residues as peptoid nucleic acid monomers. Tetrahedron 57:16, pages 3373-3381.
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Jin‐Quan Bai, Ying Li & Ke‐Liang Liu. (2010) Design and Synthesis of Novel Peptide Nucleic Acid Monomers. Chinese Journal of Chemistry 19:3, pages 276-281.
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András Földesi, Anna Trifonova, Zoltán Dinya & Jyoti Chattopadhyaya. (1999) Selective cleavage of the O6-diphenylcarbamoyl group from sugar-modified guanosines for incorporation into oligo-RNA. Tetrahedron Letters 40:40, pages 7283-7284.
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Brigitte Allart, Roger Busson, Jef Rozenski, Arthur Van Aerschot & Piet Herdewijn. (1999) Synthesis of protected D-altritol nucleosides as building blocks for oligonucleotide synthesis. Tetrahedron 55:21, pages 6527-6546.
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Michael E. Jung & Mehrak Kiankarimi. (1998) Synthesis of Methylene-Expanded 2‘,3‘-Dideoxyribonucleosides. The Journal of Organic Chemistry 63:23, pages 8133-8144.
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Ulf Diederichsen & Harald W. Schmitt. (1998) β-Homoalanyl-PNA: A Special Case of β-Peptides with β-Sheet-Like Backbone Conformation; Organization in Higher Ordered Structures. European Journal of Organic Chemistry 1998:5, pages 827-835.
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L. A. Agrofoglio & S. R. ChallandL. A. Agrofoglio & S. R. Challand. 1998. Acyclic, Carbocyclic and L-Nucleosides. Acyclic, Carbocyclic and L-Nucleosides 174 255 .
Bart De Bouvere, Luc Kerremans, Jef Rozenski, Gerard Janssen, Arthur van Aerschot, Paul Claes, Roger Busson & Piet Herdewijn. (1997) Improved Synthesis of Anhydrohexitol Building Blocks for Oligonucleotide Synthesis. Liebigs Annalen 1997:7, pages 1453-1461.
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Morris J. Robins, Ruiming Zou, Zhiqiang Guo & Stanislaw F. Wnuk. (1996) Nucleic Acid Related Compounds. 93. A Solution for the Historic Problem of Regioselective Sugar−Base Coupling To Produce 9-Glycosylguanines or 7-Glycosylguanines 1 . The Journal of Organic Chemistry 61:26, pages 9207-9212.
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Alan D. Borthwick, Andrew J. Crame, Anne M. Exall, Gordon G. Weingarten & Mahmuod Mahmoudian. (1995) A short, convergent synthesis of two chiral antiviral agents, (+) carbocyclic 2′-deoxy-5-[(E)-2-bromovinyl] uridine and (+) carbocyclic 2′-deoxyGuanosine. Tetrahedron Letters 36:38, pages 6929-6932.
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Pierre Martin. (2004) Ein neuer Zugang zu 2′‐ O ‐Alkylribonucleosiden und Eigenschaften deren Oligonucleotide . Helvetica Chimica Acta 78:2, pages 486-504.
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Christophe Bonnal, Claude Chavis & Marc Lucas. (1994) Synthesis of meso-2′,3′-dideoxy-3′β-hydroxymethyl carbocyclic nucleosides as potential antiviral drugs. Unusual competitive 2-O-versus N 1 -alkylation of 3-substituted pyrimidines under Mitsunobu conditions . J. Chem. Soc., Perkin Trans. 1:11, pages 1401-1410.
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Luigi Agrofoglio, Edouard Suhas, Audrey Farese, Roger Condom, S. Richard Challand, Robert A. Earl & Roger Guedj. (1994) Synthesis of carbocyclic nucleosides. Tetrahedron 50:36, pages 10611-10670.
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Thomas F. Jenny & Steven A. Benner. (2004) Carbocyclic Analogs of Nucleosides. Part 4. Preparation of enantiomerically pure analogs of purine nucleosides for the synthesis of sulfone‐linked oligonucleotide analogs. Helvetica Chimica Acta 76:2, pages 826-841.
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Suhaib M. Siddiqi, Frank P. Oertel, Xing Chen & Stewart W. Schneller. (1993) Enantiospecific synthesis of the fluoro and epimeric derivatives of 5′-noraristeromycin. J. Chem. Soc., Chem. Commun.:8, pages 708-709.
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Thomas F. Jenny, Jennifer Horlacher, Nicoletta Previsani & Steven A. Benner. (2004) Carbocyclic analogs of nucleosides. Part 2.. Synthesis of 2′,3′‐dideoxy‐5′‐homonucleoside analogs. Helvetica Chimica Acta 75:6, pages 1944-1954.
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Thomas F. Jenny & Steven A. Benne. (1992) Efficient regioselective synthesis of guanosine analogs. Tetrahedron Letters 33:44, pages 6619-6620.
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