C-Glycosylation of Substituted Heterocycles Under Friedel-Crafts Conditions (II): Ribosylation of Multi-Functionalized Thiophenes and Furans for the Synthesis of Purine-Like C-Nucleosides

References

• Chu , M.-Y. , Zuckerman , L. B. , Sato , S. , Crabtree , G. W. , Bogden , A. E. , Lira , M.-I. and Klein , R. S. 1984 . Biochem. Pharmacol. , 33 : 1229
   PubMed Web of Science ®Google Scholar
• Burchenal , J. H. , Leyland-Jones , B. , Watanabe , K. A. , Klein , R. S. , Lopez , C. and Fox , J. J. 1983 . “Nucleosides, Nucleotides and Their Biological Applications” , Edited by: Rideout , J. L. , Henry , D. W. and Beacham , L. M. III . 47 – 65 . New York : Academic Press Inc. .
   Google Scholar
• Glazer , R. I. , Hartman , K. D. and Knode , M. C. 1983 . Mol. Pharmacol. , 24 : 309
   PubMed Web of Science ®Google Scholar
• Ren , W.-Y. , Lira , M.-I. , Burchenal , J. H. and Klein , R. S. 1981 . 182nd National meeting of the American Chemical Society . 1981 , New York, NY. Abstr. GARB 48
   Google Scholar
• Bhattacharya , B. K. , Lira , M.-I. , Otter , B. A. and Klein , R. S. 1986 . Tetrahedron Lett. , 27 : 815
   Google Scholar
• Berman , J. D. , Hanson , W. L. , Lovelace , J. K. , Waits , V. B. , Jackson , J. E. , Chapman , W. L. Jr. and Klein , R. S. 1987 . Antimicrob. Agents Chemother. , 31 : 111
   Google Scholar
• Marr , J. J. , Berens , R. L. , Cohn , N. K. , Nelson , D. J. and Klein , R. S. 1984 . Antimicrob. Agents Chemother. , 25 : 292
   PubMed Web of Science ®Google Scholar
• Bacchi , C. J. , Berens , R. L. , Nathan , H. C. , Klein , R. S. , Elegbe , I. A. , Rao , K. V. B. , McCann , P. P. and Marr , J. J. 1987 . Antimicrob. Agents Chemother. , 31 : 1406
   PubMed Web of Science ®Google Scholar
• Bhattacharya , B. K. , Otter , B. A. , Berens , R. L. and Klein , R. S. Nucleosides and Nucleotides. (submitted)
   Google Scholar
• La Fon , S. W. , Nelson , D. J. , Berens , R. L. and Marr , J. J. 1985 . J. Biol. Chem. , 260 : 9660
   PubMedGoogle Scholar
• Fish , W. R. , Marr , J. J. , Berens , R. L. , Looker , D. L. , Nelson , D. J. , La Fon , S. W. and Balber , A. E. 1985 . Antimicrob. Agents Chemother. , 27 : 33
   PubMed Web of Science ®Google Scholar
• Smith , J. W. , Bartlett , M. S. , Queener , S. F. , Durkin , M. M. , Jay , M. A. , Hull , M. T. , Klein , R. S. and Marr , J. J. 1987 . Diagn. Microbiol. Infect. Pis. , 7 : 113
   PubMedGoogle Scholar
• Bartlett , M. S. , Marr , J. J. , Queener , S. F. , Klein , R. S. and Smith , J. W. 1986 . Antimicrob. Agents Chemother. , 30 : 181
   Google Scholar
• Berens , R. L. and Marr , J. J. 1986 . Biochem. Pharmacol. , 35 : 4191
   Google Scholar
• Stoeckler , J. D. , Ryder , J. B. , Parks , R. E. Jr. , Chu , M.-Y. , Lim , M.-I. , Ren , W.-Y. and Klein , R. S. 1986 . Cancer Research , 46 : 1774
   PubMed Web of Science ®Google Scholar
• Rao , S. P. , Rao , K. V. B. , Otter , B. A. , Klein , R. S. and Ren , W.-Y. 1988 . Tetrahedron Lett. , 29 : 3537
   Web of Science ®Google Scholar
• Bacchi , Cyrus J. Dr. New York, , USA : Pace University . Personal communication from
   Google Scholar
• Olah , G. A. 1963 . “Friedel-Crafts and Related Reactions” , Edited by: Olah , G. A. Vol. I , 201 – 366 . New York : Interscience Publishers .
   Google Scholar
• Hartough , H. D. and Kosak , A. I. 1947 . J. Am. Chem. Soc. , 69 : 3093
   Web of Science ®Google Scholar
• Sheehan , J. C. and Yang , D.-D. H. 1958 . J. Am. Chem. Soc. , 80 : 1154
   Web of Science ®Google Scholar
• Kost , D. and Egozy , H. 1989 . J. Org. Chem. , 54 : 4909
   Google Scholar
• Moriarty , R. M. 1964 . J. Org. Chem. , 29 : 2748
   Google Scholar
• Szarek , W. A. , Wolfe , S. and Jones , J. K. N. 1964 . Tetrahedron lett. , : 2743 and references therein
   Google Scholar
• The NMR spectrum of this compound shows the presence of two rotamers which was confirmed by variable temperature 1H NMR experiments in DMSO-d 6, as was done for compound 12
   Google Scholar
• Ohrui , H. , Jones , G. H. , Moffatt , J. G. , Maddox , M. L. , Christensen , A. T. and Byram , S. K. 1973 . J. Am. Chem. Soc. , 97 : 4602
   Google Scholar
• Cousineau , T. J. and Secrist , J. A. III . 1979 . J. Org. Chem. , 44 : 4351
   Web of Science ®Google Scholar
• Secrist , J. A. III . 1978 . J. Org. Chem. , 43 : 2925
   Google Scholar
• Baker , B. R. , Joseph , J. P. , Schaub , R. E. , McEvoy , F. J. and Williams , J. H. 1953 . J. Org. Chem. , 18 : 158
   Google Scholar
• Sodum , R. S. , Klein , R. S. and Otter , B. A. 1986 . J. Het. Chem. , 23 : 1239
   Google Scholar
• Edwards , J. A. , Johnson , G. R. , Beeby , P. J. and Fried , J. H. 1974 . Tetrahedron lett. , : 2031
   Google Scholar
• Albert , A. 1968 . “Heterocyclic Chemistry”, , Second Edition , 263 – 266 . University of London, The Athlone Press .
   Google Scholar
• Similar 13C NMR criteria were used to establish the site of glycosylation of the thiophene C-nucleosides. In addition to chemical shift considerations, analysis of the two- and three bond couplings of all the thiophene carbons in the N-acetyl nucleoside corresponding to deblocked 7b revealed unambiguously that the sugar is located on the carbon adjacent to the amide function (Unpublished results)
   Google Scholar