A facile and practical synthesis of peracylated 4-thio-D-ribofuranoses from D-glucose

Journal of Organic Chemistry

Volumn 73, Issue 6, 2008, Pages 2462-2465

  Sun, Zhi Hua ^a   Wang, Bing ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

REACTION KINETICS; SULFUR; SYNTHESIS (CHEMICAL);

CONSECUTIVE DISPLACEMENT REACTIONS; THIO-D-RIBOFURANOSES;

GLUCOSE;

CARBOHYDRATE DERIVATIVE; GLUCOSE; SULFUR;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; CRYSTAL STRUCTURE; DEPROTECTION REACTION; IODINATION; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

ACETATES; ACYLATION; BENZOATES; FURANS; GLUCOSE; RIBOSE;

EID: 41849084168     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7026596     Document Type: Article

References (43)

1. For examples, see: (a) Dyson, M. R.; Coe, P. L.; Walker, R. T. J. Med. Chem. 1991, 34, 2782.
2. (b) Secrist, J. A., III; Tiwari, K. N.; Riordan, J. M.; Montgomery, J. A. J. Med. Chem. 1991, 34, 2361.
3. (c) Bellon, L.; Barascut, J. L.; Imbach, J. L. Nucleosides Nucleotides 1992, 11, 1467.
4. (d) Yoshimura, Y.; Kitano, K.; Satoh, H.; Watanabe, M.; Miura, S.; Sakata, S.; Sasaki, T.; Matsuda, A. J. Org. Chem. 1996, 61, 822.
5. (e) Yoshimura, Y.; Kitano, K.; Yamada, K.; Satoh, H.; Watanabe, M.; Miura, S.; Sakata, S.; Sasaki, T.; Matsuda, A. J. Org. Chem. 1997, 62, 3140.
6. (f) Yoshimura, Y.; Endo, M.; Muira, S.; Sakata, S. J. Org. Chem. 1999, 64, 7912 and references cited therein.
7. (a) Parks, R. E., Jr.; Stoeckler, J. D.; Cambor, C.; Savarese, T. M.; Crabtree, G. W.; Chu, S.-H. In Molecular Actions and Targets for Cancer Chemotherapeutic Agents; Sartorelli, A. C., Lazo, J. S., Bertino, J. R., Eds.; Academic Press: New York, 1981; p 229.
8. (b) Rahim, S. G.; Littler, E.; Powell, K. L.; Collins, P. L.; Dyson, M. R.; Walker, R. T. Proceedings of the 31st ICAAC; Chicago, 1991; p 1232.
9. (a) Leydier, C.; Bellon, L.; Barascut, J. L.; Morvan, F.; Rayner, B.; Imbach, J. L. Antisense Res. Dev. 1995, 5, 167.
10. (b) Leydier, C.; Bellon, L.; Barascut, J. L.; Imbach, J. L. Nucleosides Nucleotides 1995, 14, 1027.
11. (c) Boggon, T. J.; Hancox, E. L.; McAuley-Hecht, K. E.; Connolly, B. A.; Hunter, W. N.; Brown, T.; Walker, R. T.; Leonard, G. A. Nucleic Acids Res. 1996, 24, 951.
12. (d) Jones, G. D.; Altmann, K.-H.; Husken, D.; Walker, R. T. Bioorg. Med. Chem. Lett. 1997, 7, 1275.
13. (a) Reist, E. J.; Gueffroy, D. E.; Goodman, L. J. Am. Chem. Soc. 1964, 86, 5658.
14. (b) Whistler, R. L.; Dick, W. E.; Ingle, T. R.; Rowell, R. M.; Urbas, B. J. Org. Chem. 1964, 29, 3723.
15. For examples, see: (a) Whistler, R. L.; Nayak, U. G.; Perkins, A. W., Jr. Chem. Commun. 1968, 1339.
16. (b) Whistler, R. L.; Nayak, U. G.; Perkins, A. W., Jr. J. Org. Chem. 1970, 35, 519.
17. (c) Jeong, L. S.; Moon, H. R.; Choi, Y. J.; Chun, M. W.; Kim, H. O. J. Org. Chem. 1998, 63, 4821.
18. (d) Satoh, H.; Yoshimura, Y.; Sakata, S.; Miura, S.; Machida, H. Bioorg. Med. Chem. Lett. 1998, 8, 989.
19. (e) Wirsching, J.; Voss, J. Eur. J. Org. Chem. 1999, 691.
20. Fu, Y.-L.; Bobek, M. J. Org. Chem. 1976, 41, 3831.
21. Varela, O.; Cicero, D.; de Lederkremer, R. M. J. Org. Chem. 1989, 54, 1884.
22. (a) Urbas, B.; Whistler, R. L. J. Org. Chem. 1966, 31, 813.
23. (b) Haeberli, P.; Berger, I.; Pallen, P. S.; Egli, M. Nucleic Acids Res. 2005, 33, 3965.
24. Naka, T.; Minakawa, N.; Abe, H.; Kaga, D.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 7233.
25. Yoshimura, Y.; Kuze, T.; Ueno, M.; Komiya, F.; Haraguchi, K.; Tanaka, H.; Kano, F.; Yamada, K.; Asami, K.; Kaneko, N.; Takahata, H. Tetrahedron Lett. 2006, 47, 591.
26. (a) Kita, Y.; Yasuda, H.; Tamura, O.; Itoh, F.; Tamura, Y. Tetrahedron Lett. 1984, 25, 4681.
27. (b) Kita, Y.; Tamura, O.; Yasuda, H.; Itoh, F.; Tamura, Y. Chem. Pharm. Bull. 1985, 33, 4235.
28. (a) Whistler, R. L.; Doner, L. W.; Nayak, U. G. J. Org. Chem. 1971, 36, 108.
29. (b) Bobek, M.; Bloch, A.; Parthasarathy, R.; Whistler, R. L. J. Med. Chem. 1975, 18, 784.
30. For simple inversion of C5 configuration by sulfur nucleophiles, see: Calvo-Flores, F. G.; García-Mendoza, P.; Hernández-Mateo, F.; Isac-García, J.; Santoyo-González, F. J. Org. Chem. 1997, 62, 3944 and references cited therein.
31. Pitsch, S. Helv. Chim. Acta 1997, 80, 2286.
32. Zheng, X.; Nair, V. Nucleosides Nucleotides 1999, 18, 1961.
33. Yuasa, H.; Tamura, J.; Hashimoto, H. J. Chem. Soc., Perkin Trans. 1 1990, 2763.
34. Hall, L. D.; Hough, L.; Pritchard, R. A. J. Chem. Soc. 1961, 1537.
35. (a) Garegg, P. J.; Samuelsson, B. J. Chem. Soc., Chem. Commun. 1979, 978.
36. (b) Garegg, P. J.; Samuelsson, B. J. Chem. Soc., Perkin Trans. 1 1980, 2866.
37. Lee, C. K.; Jiang, H.; Scofield, A. M. J. Carbohydr. Chem. 1997, 16, 49.
38. Whistler, R. L.; Gramera, R. E. J. Org. Chem. 1964, 29, 2609.
39. Egron, D.; Durand, T.; Roland, A.; Vidal, J.-P.; Rossi, J.-C. Synlett 1999, 435.
40. (a) A single example of intramolecular displacement of 5-Cl by 6-thiol to form a 5,6-thiirane has been reported: Chiu, C.-W.; Whistler, R. L. J. Org. Chem. 1973, 38, 832.
41. (b) Whistler also examined the substitution of 5-tosylate by AcSK, but the starting material was prepared in a much roundabout way; see: Nayak, U. G.; Whistler, R. L. J. Org. Chem. 1969, 34, 97.
42. David, S.; de Sennyey, G. Carbohydr. Res. 1979, 77, 79.
43. For a detailed mechanistic study, see: Hanessian, S.; Plessas, N. R. J. Org. Chem. 1969, 34, 1053. Accordingly, we observed the following results: