Synthesis of 2′-Substituted Inosine Analogs via Unusual Masking of the 6-Hydroxyl Group

REFERENCES

• Casu , F. , Chiacchio , M. A. , Romeo , R. and Gumina , G. 2007 . Chiral synthesis of heterosubstituted nucleoside analogs from non-carbohydrate precursors . Curr. Org. Chem. , 11 : 1017 – 1032 .
   Web of Science ®Google Scholar
• Casu , F. , Chiacchio , M. A. , Romeo , R. and Gumina , G. 2007 . Chiral synthesis of carbocyclic nucleoside analogs from non-carbohydrate precursors . Curr. Org. Chem. , 11 : 999 – 1016 .
   Web of Science ®Google Scholar
• Gumina , G. , Olgen , S. and Chu , C. K. 2003 . “ Chiral synthesis of antiviral nucleosides from carbohydrate templates ” . In Antiviral Nucleosides: Chiral Synthesis and Chemotherapy , Edited by: Chu , C. K. Atlanta , GA : Elsevier Science . pp. 77–189
   Google Scholar
• Gumina , G. , Choi , Y. and Chu , C. K. 2003 . “ Recent advances in antiviral nucleosides ” . In Antiviral Nucleosides: Chiral Synthesis and Chemotherapy , Edited by: Chu , C. K. Atlanta , GA : Elsevier Science . pp. 1–76
   Google Scholar
• Legrand-Abravanel , F. , Nicot , F. and Izopet , J. 2010 . New NS5B polymerase inhibitors for hepatitis C . Expert Opin. Investig. Drugs , 19 : 963 – 975 .
   PubMed Web of Science ®Google Scholar
• Carroll , S. S. and Olsen , D. B. 2006 . Nucleoside analog inhibitors of hepatitis C virus replication . Infect. Disord. Drug Targets , 6 : 17 – 29 .
   PubMedGoogle Scholar
• Vorbrüggen , H. , Krolikiewicz , K. and Niedballa , U. 1975 . Synthesis of nucleosides with use of trimethylsilyl-heterocycles . Ann. N.Y. Acad. Sci. , 255 : 82 – 90 .
   PubMed Web of Science ®Google Scholar
• Vorbrüggen , H. and Bennua , B. 1978 . New simplified nucleoside synthesis . Tetrahedron Lett. , 19 : 1339 – 1342 .
   Google Scholar
• Miller , P.S. and TS'O , P.O.P. Linkage of proteins to nucleic acids . Patent No. US 4587044, May 1986 ,
   Google Scholar
• Sauer , C. and Schwabe , U. 1980 . Method for the selective 2′-O-substitution of nucleosides . Z. Naturforsch. C: J. Biosci. , 35C : 163 – 167 .
   Google Scholar
• Pierra , C. , Benzaria , S. , Amador , A. , Moussa , A. , Mathieu , S. , Storer , R. and Gosselin , G. 2005 . NM 283, an efficient prodrug of the potent anti-HCV agent 2′-C-methylcytidine . Nucleosides Nucleotides Nucleic Acids , 24 : 767 – 770 .
   PubMed Web of Science ®Google Scholar
• Eldrup , A. B. , Allerson , C. R. , Bennett , C. F. , Bera , S. , Bhat , B. , Bhat , N. , Bosserman , M. R. , Brooks , J. , Burlein , C. , Carroll , S. S. , Cook , P. D. , Getty , K. L. , MacCoss , M. , McMasters , D. R. , Olsen , D. B. , Prakash , T. P. , Prhavc , M. , Song , Q. L. , Tomassini , J. E. and Xia , J. 2004 . Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase . J. Med. Chem. , 47 : 2283 – 2295 .
   PubMed Web of Science ®Google Scholar
• Carroll , S. , Tomassini , J. E. , Bosserman , M. , Getty , K. , Stahlhut , M. W. , Eldrup , A. B. , Bhat , B. , Hall , D. , Simcoe , A. L. , LaFemina , R. , Rutkowski , C. A. , Wolanski , B. , Yang , Z. , Migliaccio , G. , De Francesco , R. , Kuo , L. C. , MacCoss , M. and Olsen , D. B. 2003 . Inhibition of hepatitis C virus RNA replication by 2′-modified nucleoside analogs . J. Biol. Chem. , 278 : 11979 – 11984 .
   PubMed Web of Science ®Google Scholar
• Gundlach , C. W. IV , Ryder , T. R. and Glick , G. D. 1997 . Synthesis of guanosine analogs bearing pendant alkylthiol tethers . Tetrahedron Lett. , 38 : 4039 – 4042 .
   Web of Science ®Google Scholar
• Grøtli , M. , Douglas , M. , Beijer , B. , García , R. G. , Eritja , R. and Sproat , B. 1997 . Protection of the guanine residue during synthesis of 2′-O-alkylguanosine derivatives . J. Chem. Soc. Perkin Trans. 1 , 18 : 2779 – 2786 .
   Google Scholar
• Markiewicz , W. T. 1979 . Tetraisopropyldisiloxane-1,3-diyl, a group for simultaneous protection of 3′- and 5′-hydroxy functions of nucleosides . J. Chem. Res. Synop. , : 24 – 25 .
   Web of Science ®Google Scholar
• Beijer , B. , Grøtli , M. , Douglas , M. E. and Sproat , B. S. 1994 . Simplified and cost effective syntheses of fully protected phosphoramidite monomers suitable for the assembly of oligo(2′-O-allylribonucleotides) . Nucleosides Nucleotides , 13 : 1905 – 1927 .
   Google Scholar
• Wada , T. , Tobe , M. , Nagayama , T. , Furusawa , K. and Sekine , M. 1995 . Regioselective protection of the 2′-hydroxyl group of N-acyl-3′,5′-O-di(t-butyl) silanediylnucleoside derivatives by use of t-BuMgCl and 2-(trimethylsilyl) ethoxymethyl chloride . Tetrahedron Lett. , 36 : 1683 – 1684 .
   Web of Science ®Google Scholar
• Grøtli , M. , Douglas , M. , Beijer , B. , Eritja , R. and Sproat , B. 1997 . A simple method for the synthesis of 2′-O-alkylguanosine derivatives . Bioorg. Med. Chem. Lett. , 7 : 425 – 428 .
   Web of Science ®Google Scholar
• Chow , S. , Wen , K. , Sanghvi , Y. S. and Theodorakis , E. A. 2003 . MDPSCL2: A new protecting group for chemoselective synthesis of 2′-O-alkylated guanosines . Nucleosides Nucleotides Nucleic Acids , 22 : 583 – 587 .
   PubMed Web of Science ®Google Scholar
• Chow , S. , Wen , K. , Sanghvi , Y. S. and Theodorakis , E. A. 2003 . Novel synthesis of 2′-O-methylguanosine . Bioorg. Med. Chem. Lett. , 13 : 1631 – 1634 .
   PubMed Web of Science ®Google Scholar
• Wen , K. , Chow , S. , Sanghvi , Y. S. and Theodorakis , E. A. 2002 . Synthesis of 2′-O-methoxyethylguanosine using a novel silicon-based protecting group . J. Org. Chem. , 67 : 7887 – 7889 .
   PubMed Web of Science ®Google Scholar
• Haraguchi , K. , Nishikawa , A. , Sasakura , E. , Tanaka , H. , Nakamura , K. T. and Miyasaka , T. 1998 . Electrophilic addition to 4-thio furanoid glycal: A highly stereoselective entry to 2′-deoxy-4′-thio pyrimidine nucleosides . Tetrahedron Lett. , 39 : 3713 – 3716 .
   Web of Science ®Google Scholar
• Purdy , D. F. , Zintek , L. B. and Nair , V. 1994 . Synthesis of isonucleosides related to AZT and AZU . Nucleosides Nucleotides , 13 : 109 – 126 .
   Google Scholar
• Robins , M. J. , Samano , V. , Zhang , W. , Balzarini , J. , De Clercq , E. , Borchardt , R. T. , Lee , Y. and Yuan , C. S. 1992 . Nucleic acid related compounds. 74. Synthesis and biological activity of 2′(and 3′)-deoxy-2′(and 3′)-methylenenucleoside analogs that function as mechanism-based inhibitors of S-adenosyl-L-homocysteine hydrolase and/or ribonucleotide reductase . J. Med. Chem. , 35 : 2283 – 2293 .
   PubMed Web of Science ®Google Scholar
• Nishino , S. , Takamura , H. and Ishido , Y. 1986 . Regioselective protection of carbohydrate derivatives: Part. 20 simple, efficient 2′-o-deacylation of fully acylated purine and pyrimidine ribonucleosides through tert-butoxide . Tetrahedron , 42 : 1995 – 2004 .
   Web of Science ®Google Scholar
• Bordon-Pallier , F. and Haesslein , J.–L. Process for preparation of new purine derivatives, their application as drugs, pharmaceutical compositions containing them, and new uses for them . Periodic No. FR 2851248, 20 August 2004
   Google Scholar
• Agarwal , A. and Chauhan , P. 2004 . Convenient dimethylamino amination in heterocycles and aromatics with dimethylformamide . Synth. Commun. , 34 : 2925 – 2930 .
   Web of Science ®Google Scholar
• Abramov , M. , Marchand , A. , Calleja-Marchand , A. and Herdewijn , P. 2004 . Synthesis of D-altritol nucleosides with a 3′-O-tert-butyldimethylsilyl protecting group . Nucleosides Nucleotides Nucleic Acids , 23 : 439 – 455 .
   PubMed Web of Science ®Google Scholar
• Coppinger , G. M. 1954 . Preparations of N,N-dimethylamides . J. Am. Chem. Soc. , 76 : 1372 – 1373 .
   Web of Science ®Google Scholar
• Deorha , D. S. and Sharma , H. L. 1963 . Reaction of halonitrobenzenes with dimethylformamide . J. Ind. Chem. Soc. , 40 : 819 – 820 .
   Google Scholar
• Liu , J. , Janeba , Z. and Robins , M. J. 2004 . SNAr Iodination of 6-Chloropurine Nucleosides: Aromatic Finkelstein reactions at temperatures below −40°C . Org. Lett. , 6 : 2917 – 2919 .
   PubMed Web of Science ®Google Scholar