Synthesis of 9-[2',3'-dideoxy-2',3'-bis-C-hydroxymethyl-α-L-threofuranosyl] adenine and its 4'-thio analog as potential antiviral agents

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4795-4798

  Kikuchi, Yoshiko ^a   Kurata, Hiroko ^a   Nishiyama, Shigeru ^a   Yamamura, Shosuke ^a   Kato, Kuniki ^b  

^a KEIO UNIVERSITY   (Japan)

^b NIPPON KAYAKU CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; NUCLEOSIDE DERIVATIVE; OXETANOCIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0031000301     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01035-6     Document Type: Article

References (23)

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15. Dyson, M. R.; Coe, P. L.; Walker, R. T. J. Med. Chem. 1991, 34, 2782-2786. Secrist III, J. A.; Tiwari, K. N.; Riordan, J. M.; Montgomery, J. A. J. Med. Chem. 1991, 34, 2361-2366. Van Draanen, N. A.; Freeman, G. A.; Short, S. A.; Harvey, R.; Jansen, R.; Szczech, G.; Koszalka, G. W. J. Med. Chem. 1996, 39, 538-542. Rahim, S. G.; Trivedi, N.; Bogunovic-Batchelor, M. V.; Hardy, G. W.; Mills, G.; Selway, J. W. T.; Snowden, W.; Littler, E.; Coe, P. L.; Basnak, I.; Whale, R. E.; Walker, R. T. J. Med. Chem. 1996, 39, 789-795.
16. Dyson, M. R.; Coe, P. L.; Walker, R. T. J. Med. Chem. 1991, 34, 2782-2786. Secrist III, J. A.; Tiwari, K. N.; Riordan, J. M.; Montgomery, J. A. J. Med. Chem. 1991, 34, 2361-2366. Van Draanen, N. A.; Freeman, G. A.; Short, S. A.; Harvey, R.; Jansen, R.; Szczech, G.; Koszalka, G. W. J. Med. Chem. 1996, 39, 538-542. Rahim, S. G.; Trivedi, N.; Bogunovic-Batchelor, M. V.; Hardy, G. W.; Mills, G.; Selway, J. W. T.; Snowden, W.; Littler, E.; Coe, P. L.; Basnak, I.; Whale, R. E.; Walker, R. T. J. Med. Chem. 1996, 39, 789-795.
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18. After many trials we decided on the use of an allyl group to effect an inversion reaction via a triflate. When an acetyl or MOM (methoxymethyl) group was used as a protecting group, respectively, the triflate was very unstable.
19. Norweck, D. W.; Spanton, S.; Broder, S.; Mitsuya, H. Tetrahedron Lett. 1989, 30, 6263-6266.
20. The O-benzoate group branching out of C-2 in compound 17 is capable of directing a preferred α-face attack via a cyclic six-membered 1, 3 ortho ester ion. Similar control of stereochemistry by such participation reaction has been reported by Marquez et al (see ref 4).
21. 1H NMR and/or reversed-phase HPLC.
22. +), found 281.0953.
23. Evaluation of compounds 26 and 28 against HSV-1 and HSV-2 in Vero cells by a plaque reduction assay at concentrations up to 10 μg/ml, and HIV-1 in MT-4 cells by an indirect immunofluorescence assay at concentrations up to 10 μg/ml revealed these compounds to be devoid of antiviral activity and cytotoxicity.