A novel synthesis of new antineoplastic 2′-deoxy-2′-substituted-4′-thiocytidines

Journal of Organic Chemistry

Volumn 61, Issue 3, 1996, Pages 822-823

  Yoshimura, Yuichi ^a   Kitano, Kenji ^a   Satoh, Hiroshi ^a   Watanabe, Mikari ^a   Miura, Shinji ^a   Sakata, Shinji ^a   Sasaki, Takuma ^b   Matsuda, Akira ^c  

^a YAMASA CORPORATION   (Japan)

^b KANAZAWA UNIVERSITY   (Japan)

^c HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001023643     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9519423     Document Type: Article

References (26)

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15. Uenishi and his co-workers reported an elegant synthesis of 2′-deoxy-4′-thionucleosides using Sharpless asymmetric epoxidation: (a) Uenishi, J ; Motoyama, M.; Nishiyama, Y.; Wakabayashi, S. J. Chem. Soc. Chem. Commun. 1991, 1421-1422. (b) Uenishi, J.; Takahashi, K.; Motoyama, M.; Akashi, H.; Sasaki, T. Nucleosides Nucleotides 1994, 13, 1347-1361.
16. Uenishi and his co-workers reported an elegant synthesis of 2′-deoxy-4′-thionucleosides using Sharpless asymmetric epoxidation: (a) Uenishi, J ; Motoyama, M.; Nishiyama, Y.; Wakabayashi, S. J. Chem. Soc. Chem. Commun. 1991, 1421-1422. (b) Uenishi, J.; Takahashi, K.; Motoyama, M.; Akashi, H.; Sasaki, T. Nucleosides Nucleotides 1994, 13, 1347-1361.
17. Fluorine substituted derivatives and dideoxy analogues, including AZT, of 4′-thionucleosides were reported. Fluorine substituted derivatives: (a) Jeng, L. S.; Nicklaus, M. C.; George, C.; Marquez, V. E. Tetrahedron Lett. 1994, 35, 7569-7572. (b) Jeng, L. S., Nicklaus, M. C.; George, C.; Marquez, V. E. Tetrahedron Lett. 1994, 35, 7573-7576. Dideoxy derivatives: (c) Secrist, J. A.; Riggs, R. M.; Tiwari, K. N.; Montgomery, J. A. J. Med. Chem. 1992, 35, 533-538. (d) Tber, B.; Fahmi, N.-E.; Ronco, G.; Villa, P.; Ewing, D. F.; Mackenzie, G. Carbohydr. Res. 1995, 267, 203-215.
18. Fluorine substituted derivatives and dideoxy analogues, including AZT, of 4′-thionucleosides were reported. Fluorine substituted derivatives: (a) Jeng, L. S.; Nicklaus, M. C.; George, C.; Marquez, V. E. Tetrahedron Lett. 1994, 35, 7569-7572. (b) Jeng, L. S., Nicklaus, M. C.; George, C.; Marquez, V. E. Tetrahedron Lett. 1994, 35, 7573-7576. Dideoxy derivatives: (c) Secrist, J. A.; Riggs, R. M.; Tiwari, K. N.; Montgomery, J. A. J. Med. Chem. 1992, 35, 533-538. (d) Tber, B.; Fahmi, N.-E.; Ronco, G.; Villa, P.; Ewing, D. F.; Mackenzie, G. Carbohydr. Res. 1995, 267, 203-215.
19. Fluorine substituted derivatives and dideoxy analogues, including AZT, of 4′-thionucleosides were reported. Fluorine substituted derivatives: (a) Jeng, L. S.; Nicklaus, M. C.; George, C.; Marquez, V. E. Tetrahedron Lett. 1994, 35, 7569-7572. (b) Jeng, L. S., Nicklaus, M. C.; George, C.; Marquez, V. E. Tetrahedron Lett. 1994, 35, 7573-7576. Dideoxy derivatives: (c) Secrist, J. A.; Riggs, R. M.; Tiwari, K. N.; Montgomery, J. A. J. Med. Chem. 1992, 35, 533-538. (d) Tber, B.; Fahmi, N.-E.; Ronco, G.; Villa, P.; Ewing, D. F.; Mackenzie, G. Carbohydr. Res. 1995, 267, 203-215.
20. Fluorine substituted derivatives and dideoxy analogues, including AZT, of 4′-thionucleosides were reported. Fluorine substituted derivatives: (a) Jeng, L. S.; Nicklaus, M. C.; George, C.; Marquez, V. E. Tetrahedron Lett. 1994, 35, 7569-7572. (b) Jeng, L. S., Nicklaus, M. C.; George, C.; Marquez, V. E. Tetrahedron Lett. 1994, 35, 7573-7576. Dideoxy derivatives: (c) Secrist, J. A.; Riggs, R. M.; Tiwari, K. N.; Montgomery, J. A. J. Med. Chem. 1992, 35, 533-538. (d) Tber, B.; Fahmi, N.-E.; Ronco, G.; Villa, P.; Ewing, D. F.; Mackenzie, G. Carbohydr. Res. 1995, 267, 203-215.
21. During the course of our investigation, the synthesis of 13 was independently reported by another group: Yuasa, H.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 8243-8246.
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24. The stereochemistry of the anomeric carbon was determined by an NOE analysis of the free nucleoside 6 (minor isomer). It showed 7.1% NOE at the H-3′ proton when irradiated at H-6.
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26. The stereochemistry at the 1′-position was determined, after deprotection, by comparison of coupling constants of H-1′ with that of gemcitabin described in ref 7a.