Synthesis of Chiral 11, 21-Seco-Nucleosides of Guanine and Uracil

Nucleosides and Nucleotides

Volumn 8, Issue 2, 1989, Pages 201-211

  Vemishetti, Purushotham ^a   Abushanab, Elie ^a   Leiby, Robert W ^a   Panzica, Raymond P ^a  

^a UNIVERSITY OF RHODE ISLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACICLOVIR; ANTIVIRUS AGENT; GUANINE; NUCLEOTIDE DERIVATIVE; URACIL;

NONHUMAN;

EID: 0024591735     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328318908054168     Document Type: Article

References (16)

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2. For a recent review see, C. K. Chu and S. J. Cutler, J. Heterocycl Chem., 1986, 23, 289.
3. H. J. Schaeffer, in “Nucleosides, Nucleotides and Their Biological Applications” J. L. Rideout, D. W. Henry, and L, M. Beacham, eds. Academic Press, New York, 1983, pp. 117.
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6. W. T. Ashton, L. F. Canning, G. F. Reynolds, R. L. Tolman, J. D. Karkas, R. Lion M. E. M. Davies, C. M. DeWitt, H. C. Perry, and A. K. Field, J. Med. Chem., 1985, 28, 926.
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9. M. MacCoss, R. L. Tolman, W. T. Ashton, A. F. Wagner, J. Hannah, A. K. Field, J. D. Karkas, and J. I. Germershausen, Chemica Scripta, 1986, 26, 113. (b) M. MacCoss, A. Chen, and R. L. Tolman, Tetrahedron Lett., 1985, 26 1815. (c) M. MacCoss, A. Chen, and R. L. Tolman, Tetrahedron Lett., 1985, 26, 4287.
10. 9-(1,3,4-Trihydroxy-2-butoxymethyl)guanine, was described by H. J. Schaeffer, ref. 3, but neither the experimental details nor the stereochemistry were given.
11. E. Abushanab, P. Vemishetti, R. W. Leiby, H. K. Singh, A. B. Mikkilineni, D. C.-J. Wu, R. Saibaba, and R. P. Panzica, J. Org. Chem., 1988, in press.
12. P. Vemishetti, R. W. Leiby, E. Abushanab, and R. P. Panzica, J. Heterocyclic Chem., 1988, in press.
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14. If after 23 h the reaction was worked up, 9-[(l,3S,4-tribenzyloxy-9c 2R-butoxy)methyl]guanine was the product. This material was 25crystallized from absolute ethanol {mp 168-170°C; [α]D=-3.56 (c = 0.90, MeOH) | and was identical (tic and 1H NMR) to an authentic sample provided by Drs. M. MacCoss and R. L. Tolman (Merck).
15. K. K. Ogilvie and H. R. Hanna, Can. J. Chem., 1984, 62, 2702.
16. J. Kjellberg and N. G. Johansson, Tetrahedron, 1986, 42, 6541.