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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 9
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Original Articles

Mitsunobu Reactions for the Synthesis of Carbocyclic Analogues of Nucleosides: Examination of the Regioselectivity1

Akemi Toyota Pharmaceutical Institute, Tohoku University, Aobayama, Sendai, 980, Japan
,
Nobuya Katagiri Pharmaceutical Institute, Tohoku University, Aobayama, Sendai, 980, Japan
&
Chikara Kaneko Pharmaceutical Institute, Tohoku University, Aobayama, Sendai, 980, Japan
Pages 1295-1305 | Received 01 Oct 1992, Published online: 24 Sep 2006

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Harikrishna Tumma, N. Nagaraju & K. Vijayakumar Reddy. (2010) N-Alkylation of 2,6-Dichloropurine Hydrochloride with a Variety of Alcohols over Alumina Catalyst. Synthetic Communications 40:12, pages 1856-1866.
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ShawnC. Miller, JamesR. McCarthy & JeffreyS. Sabol. (1998) Terminal Fluoroolefins. The Synthesis of Novel Carboacyclic Nucleosides. Nucleosides and Nucleotides 17:6, pages 1099-1113.
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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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TimothyT. Curran. (1996) An Unanticipated Result in the Pd (0) Catalyzed Coupling of Sodium Adenate with cis-4-Acetyloxy- and cis-4-t-Butyldimethylsilyloxy-2-Cyclopentenyl Diethylphosphate. Synthetic Communications 26:6, pages 1209-1221.
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Articles from other publishers (27)

Armands Sebris, Irina Novosjolova & Māris Turks. (2022) Synthesis of 7-Arylpurines from Substituted Pyrimidines. Synthesis 54:24, pages 5529-5539.
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Armands Sebris, Irina Novosjolova, Kaspars Traskovskis, Valdis Kokars, Natalija Tetervenoka, Aivars Vembris & Ma̅ris Turks. (2022) Photophysical and Electrical Properties of Highly Luminescent 2/6-Triazolyl-Substituted Push–Pull Purines. ACS Omega 7:6, pages 5242-5253.
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Cigdem Karaaslan, Fatima Doganc, Mehmet Alp, Asli Koc, Arzu Zeynep Karabay & Hakan Göker. (2020) Regioselective N-alkylation of some imidazole-containing heterocycles and their in vitro anticancer evaluation. Journal of Molecular Structure 1205, pages 127673.
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Tushar Mahajan, Mari Ytre-Arne, Pernille Strøm-Andersen, Bjørn Dalhus & Lise-Lotte Gundersen. (2015) Synthetic Routes to N-9 Alkylated 8-Oxoguanines; Weak Inhibitors of the Human DNA Glycosylase OGG1. Molecules 20:9, pages 15944-15965.
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Nadège Boudet, Srinivas Reddy Dubbaka & Paul Knochel. (2008) Oxidative Amination of Cuprated Pyrimidine and Purine Derivatives. Organic Letters 10:9, pages 1715-1718.
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Tomáš Tobrman, Petr Štěpnička, Ivana Císařová & Dalimil Dvořák. (2008) Preparation and Crystal Structures of ­Purine 2,2′-, 6,6′-, and 8,8′-Dimers. European Journal of Organic Chemistry 2008:12, pages 2167-2174.
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Christiaan W. van der Westhuyzen, Amanda L. Rousseau & Christopher J. Parkinson. (2007) Effect of substituent structure on pyrimidine electrophilic substitution. Tetrahedron 63:25, pages 5394-5405.
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Franck Amblard, Steven P. Nolan & Luigi A. Agrofoglio. (2005) Metathesis strategy in nucleoside chemistry. Tetrahedron 61:30, pages 7067-7080.
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Chieko Takagi, Makoto Sukeda, Hye-Sook Kim, Yusuke Wataya, Saori Yabe, Yukio Kitade, Akira Matsuda & Satoshi Shuto. (2005) Synthesis of 5′-methylenearisteromycin and its 2-fluoro derivative with potent antimalarial activity due to inhibition of the parasite S-adenosylhomocysteine hydrolase1. Org. Biomol. Chem. 3:7, pages 1245-1251.
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Franco Fernández, Xerardo García-Mera, Melvin Morales, Leonardo Vilariño, Olga Caamaño & Eric De Clercq. (2004) Synthesis of new 6-substituted purinyl-5′-nor-1′-homocarbanucleosides based on indanol. Tetrahedron 60:41, pages 9245-9253.
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Daniel E. Levy, Ming Bao, Diana B. Cherbavaz, James E. Tomlinson, David M. Sedlock, Charles J. Homcy & Robert M. Scarborough. (2003) Metal Coordination-Based Inhibitors of Adenylyl Cyclase:  Novel Potent P-Site Antagonists. Journal of Medicinal Chemistry 46:11, pages 2177-2186.
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Paymaneh Y.F Deghati, Alice Borghini, Adrianus M.C.H van den Nieuwendijk, Miriam Dissen-de Groote & Adriaan P IJzerman. (2003) Inhibition of nucleoside transport By new analogues of nitrobenzylthioinosine. Bioorganic & Medicinal Chemistry 11:6, pages 899-908.
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Isabelle Gillaizeau, Steve Charamon & Luigi A Agrofoglio. (2001) Enantioselective synthesis of carba- l -furanose precursors of carbanucleosides, using ring-closing metathesis. Tetrahedron Letters 42:50, pages 8817-8819.
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Ian D. Jenkins & Oyo Mitsunobu. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Henrik Franzyk, Jon Holbech Rasmussen, Raffaele Antonio Mazzei & Søren Rosendal Jensen. (1998) Synthesis of Carbocyclic Homo-N-Nucleosides from Iridoids. European Journal of Organic Chemistry 1998:12, pages 2931-2935.
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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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Ulf Diederichsen & Harald W. Schmitt. (1998) β-Homoalanyl-PNAs: Synthese und Hinweise auf Überstrukturen. Angewandte Chemie 110:3, pages 312-315.
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Ingrid Luyten & Piet Herdewijn. (1996) Synthesis and conformational behavior of purine and pyrimidine β-d-threo-hex-3'-enopyranosyl nucleosides. Tetrahedron 52:27, pages 9249-9262.
Crossref
Geir Langli, Lise-Lotte Gundersen & Frode Rise. (1996) Regiochemistry in Stille couplings of 2,6-dihalopurines. Tetrahedron 52:15, pages 5625-5638.
Crossref
Alex F. Drake, Antonio Garofalo, Jennifer M. L. Hillman, Valeria Merlo, Ray McCague & Stanley M. Roberts. (1996) Preparation of carbocyclic analogues of 2′-deoxyribonucleotides possessing a phosphonate substituent at the 5′-position. J. Chem. Soc., Perkin Trans. 1:22, pages 2739-2745.
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Åsa Rosenquist, Ingemar Kvarnström, Björn Classon & Bertil Samuelsson. (1996) Synthesis of Enantiomerically Pure Bis(hydroxymethyl)-Branched Cyclohexenyl and Cyclohexyl Purines as Potential Inhibitors of HIV. The Journal of Organic Chemistry 61:18, pages 6282-6288.
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María-Jesús Pérez-Pérez, Bogdan Doboszewski, Jef Rozenski & Piet Herdewijn. (1995) Stereocontrolled synthesis of phosphonate derivatives of tetrahydro- and dihydro-2H-pyranyl nucleosides: The selectivity of the Ferrier rearrangement. Tetrahedron: Asymmetry 6:4, pages 973-984.
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Lise-Lotte Gundersen, Geir Langli & Frode Rise. (1995) Regioselective Pd-mediated coupling between 2,6-dichloropurines and organometallic reagents. Tetrahedron Letters 36:11, pages 1945-1948.
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Maurizio Botta, Raffaele Saladino, Gabriella Gentile, Vincenzo Summa, Rosario Nicoletti, Annalisa Verri, Federico Focher & Silvio Spadari. (1994) Researches on antiviral agents. 4. Studies on the chemistry of 6-methyl-2-methoxy-4-O-acyloxy and 6-methyl-2,4-di-O-acyloxypyrimidine derivatives as new acylation reagents and inhibitors of uracil DNA glycosylases.. Tetrahedron 50:11, pages 3603-3618.
Crossref
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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Lise-Lotte Gundersen, Anne Kristin Bakkestuen, Arne Jørgen Aasen, Herald Øver»s & Frode Rise. (1994) 6-Halopurines in palladium-catalyzed coupling with organotin and organozinc reagents. Tetrahedron 50:32, pages 9743-9756.
Crossref
A. TOYOTA, N. KATAGIRI & C. KANEKO. (2010) ChemInform Abstract: Synthesis of Nucleosides and Related Compounds. Part 30. Mitsunobu Reactions for the Synthesis of Carbocyclic Analogues of Nucleosides: Examination of the Regioselectivity.. ChemInform 24:47.
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