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DOI: 10.1055/s-0032-1317713
A Simple Synthesis of 2′-Deoxy-3′-Thioinosine and Its Phosphorothioamidite
Publikationsverlauf
Received: 10. Juli 2012
Accepted after revision: 09. November 2012
Publikationsdatum:
11. Dezember 2012 (online)
Abstract
5′-O-{[Bis(4-methoxyphenyl)(phenyl)methyl])-2′-deoxy-3′-thioinosine and its S-phosphorothioamidite were prepared in five and six steps, respectively, from commercially available 2′-deoxyinosine. The key 3′-thio intermediate was synthesized by two sequential configuration inversions: a one-pot oxidation/reduction reaction and an SN2 reaction. This intermediate was readily converted into the target compound with a high yield. Compared with other methods, this synthetic strategy has the advantages of brief reaction steps, a relatively high overall yield, and regioselectivity for the configuration inversions. The products might be useful as intermediates for the preparation of new functionalized nucleosides.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1 Piccirilli JA, Vyle JS, Caruthers MH, Cech TR. Nature (London) 1993; 361: 85
- 2a Thibaudeau C, Plavec J, Garg N, Papchikhin A, Chattopadhyaya J. J. Am. Chem. Soc. 1994; 116: 4038
- 2b Plavec J, Thibaudeau C, Chattopadhyaya J. J. Am. Chem. Soc. 1994; 116: 6558
- 3a Liu X, Reese CB. Tetrahedron Lett. 1996; 37: 925
- 3b Weinstein LB, Earnshaw DJ, Cosstick R, Cech TR. J. Am. Chem. Soc. 1996; 118: 10341
- 4 Gordon PM, Sontheimer EJ, Piccirilli JA. RNA 2000; 6: 199
- 5 Szewczak AA, Kosek AB, Piccirilli JA, Strobel SA. Biochemistry 2002; 41: 2516
- 6a Butora G, Kenski DM, Cooper AJ, Fu W, Qi N, Li JJ, Flanagan WM, Davies IW. J. Am. Chem. Soc. 2011; 133: 16766
- 6b Kannan A, Burrows CJ. J. Org. Chem. 2010; 76: 720
- 6c Wunderlich CH, Spitzer R, Santner T, Fauster K, Tollinger M, Kreutz C. J. Am. Chem. Soc. 2012; 134: 7558
- 7 Beevers AP. G, Fettes KJ, O’Neil IA, Roberts SM, Arnold JR. P, Cosstick R, Fisher J. Chem. Commun. (Cambridge) 2002; 1458
- 8a Sabbagh G, Fettes KJ, Gosain R, O’Neil IA, Cosstick R. Nucleic Acids Res. 2004; 32: 495
- 8b Ariza X, Bou V, Vilarrasa J. J. Am. Chem. Soc. 1995; 117: 3665
- 8c Terrazas M, Ariza X, Farràs J, Guisado-Yang JM, Vilarrasa J. J. Org. Chem. 2004; 69: 5473
- 8d Terrazas M, Ariza X, Vilarrasa J. Org. Lett. 2005; 7: 2477
- 9 Lu J, Li N.-S, Sengupta RN, Piccirilli JA. Bioorg. Med. Chem. 2008; 16: 5754
- 10a Martin FH, Castro MM, Aboul-ela F, Tinoco I. Nucleic Acids Res. 1985; 13: 8927
- 10b Kawase Y, Iwai S, Inoue H, Miura K, Ohtsuka E. Nucleic Acids Res. 1986; 14: 7727
- 10c Ohtsuka E, Matsuki S, Ikehara M, Takahashi Y, Matsubara K. J. Biol. Chem. 1985; 260: 2605
- 11 Case-Green SC, Southern EM. Nucleic Acids Res. 1994; 22: 131
- 12 Challa H, Bruice TC. Bioorg. Med. Chem. 2004; 12: 1475
- 13 Hansske F, Madej D, Robins MJ. Tetrahedron 1984; 40: 125
- 14a Bae S, Lakshman MK. J. Am. Chem. Soc. 2007; 129: 782
- 14b Seela F, Kaiser K. Nucleic Acids Res. 1986; 14: 1825
- 14c Hansen AS, Thalhammer A, El-Sagheer AH, Brown T, Schofield CJ. Bioorg. Med. Chem. Lett. 2011; 21: 1181
- 14d Lakshman MK, Bae S. WO 2008045535 2008 ; Chem. Abstr. 2008, 148, 449867.
- 15 Eisenhuth R, Richert C. J. Org. Chem. 2008; 74: 26
- 16 Xiao P, Bai Y, Chen J, Lu Z. CN 102180926 2011 ; Chem. Abstr. 2011, 155, 484417.