Nucleosides and Nucleotides. 156. Chelation-Controlled and Nonchelation-Controlled Diastereofacial Selective Thiophenol Addition Reactions at the 2′-Position of 2′-[(Alkoxycarbonyl)methylene]-2′-deoxyuridines: Conversion of (Z)-2′-[(Alkoxycarbonyl)methylene]-2′-deoxyuridines into Their (E)-Isomers

Journal of Organic Chemistry

Volumn 62, Issue 1, 1997, Pages 11-17

  Hassan, Abdalla E A ^a   Shuto, Satoshi ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYURIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHELATION; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031021990     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9613601     Document Type: Article

References (46)

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14. Radical-stabilizing effect of carbonyl groups has been known: (a) Beckwith, A. L. J.; Gream, G. E.; Struble, D. L. Aust. J. Chem. 1972, 25, 1081. (b) Julia, M. Pure Appl. Chem. 1967, 15, 167.
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16. For references of the conjugate addition of thiolates to α,β-unsaturated esters see: (a) Kuwajima, I.; Murobushi, T.; Nakamura, E. Synthesis 1978, 602. (b) Kobayashi, N.; Iwai, K. J. Org. Chem. 1981, 46, 1823. (c) Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 363. (d) Kamimura, A.; Ono, N. J. Chem. Soc., Chem. Commun. 1988, 1278. (e) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579 and references cited therein.
17. For references of the conjugate addition of thiolates to α,β-unsaturated esters see: (a) Kuwajima, I.; Murobushi, T.; Nakamura, E. Synthesis 1978, 602. (b) Kobayashi, N.; Iwai, K. J. Org. Chem. 1981, 46, 1823. (c) Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 363. (d) Kamimura, A.; Ono, N. J. Chem. Soc., Chem. Commun. 1988, 1278. (e) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579 and references cited therein.
18. For references of the conjugate addition of thiolates to α,β-unsaturated esters see: (a) Kuwajima, I.; Murobushi, T.; Nakamura, E. Synthesis 1978, 602. (b) Kobayashi, N.; Iwai, K. J. Org. Chem. 1981, 46, 1823. (c) Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 363. (d) Kamimura, A.; Ono, N. J. Chem. Soc., Chem. Commun. 1988, 1278. (e) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579 and references cited therein.
19. For references of the conjugate addition of thiolates to α,β-unsaturated esters see: (a) Kuwajima, I.; Murobushi, T.; Nakamura, E. Synthesis 1978, 602. (b) Kobayashi, N.; Iwai, K. J. Org. Chem. 1981, 46, 1823. (c) Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 363. (d) Kamimura, A.; Ono, N. J. Chem. Soc., Chem. Commun. 1988, 1278. (e) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579 and references cited therein.
20. For references of the conjugate addition of thiolates to α,β-unsaturated esters see: (a) Kuwajima, I.; Murobushi, T.; Nakamura, E. Synthesis 1978, 602. (b) Kobayashi, N.; Iwai, K. J. Org. Chem. 1981, 46, 1823. (c) Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 363. (d) Kamimura, A.; Ono, N. J. Chem. Soc., Chem. Commun. 1988, 1278. (e) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579 and references cited therein.
21. Hansske, F.; Madej, D.; Robins, M. J. Tetrahedron 1984, 40, 125.
22. 1H NMR spectrum, even at elevated temperatures. This implies that this facial selectivity is not related to the thermodynamic stability of the two adducts.
23. A preferential α-selective hydride attack at the (ethoxycarbonyl)-methylene moiety of 5 was observed upon treatment with NaBH4 in MeOH. See: Ueda, T.; Shuto, S.; Sato, M.; Inoue, H. Nucleosides Nucleotides 1985, 4, 401.
24. For examples of the hydride reduction of 4 see: (a) ret 7. (b) Hansske, F.; Robins, M. J. J. Am. Chem. Soc. 1983, 105, 6736.
25. For examples of the hydride reduction of 4 see: (a) ret 7. (b) Hansske, F.; Robins, M. J. J. Am. Chem. Soc. 1983, 105, 6736.
26. For examples on the α-facial selective addition of carbon nucleophiles to 2′-keto-pyrimidine nucleosides see: (a) Matsuda, A.; Itoh, H.; Takenuki, K.; Sasaki, T.; Ueda, T. Chem. Pharm. Bull. 1988, 36, 945. (b) Awano, H.; Shuto, S.; Baba, M.; Kira, T.; Shigeta, S.; Matsuda, A. BioMed. Chem. Lett. 1994, 4, 367. (c) Iino, T.; Yoshimura, Y.; Matsuda, A. Tetrahedron 1994, 50, 10397. (d) Ueda, T.; Shuto, S.; Inoue, H. Nucleosides Nucleotides 1984, 3, 173. (e) Yoshimura, Y.; Saitoh, K.; Ashida, N.; Sakata, S.; Matsuda, A. BioMed. Chem. Lett. 1994, 4, 721. (f) Takenuki, K.; Itoh, H.; Matsuda, A.; Ueda, T. Chem. Pharm. Bull. 1990, 38, 2947.
27. For examples on the α-facial selective addition of carbon nucleophiles to 2′-keto-pyrimidine nucleosides see: (a) Matsuda, A.; Itoh, H.; Takenuki, K.; Sasaki, T.; Ueda, T. Chem. Pharm. Bull. 1988, 36, 945. (b) Awano, H.; Shuto, S.; Baba, M.; Kira, T.; Shigeta, S.; Matsuda, A. BioMed. Chem. Lett. 1994, 4, 367. (c) Iino, T.; Yoshimura, Y.; Matsuda, A. Tetrahedron 1994, 50, 10397. (d) Ueda, T.; Shuto, S.; Inoue, H. Nucleosides Nucleotides 1984, 3, 173. (e) Yoshimura, Y.; Saitoh, K.; Ashida, N.; Sakata, S.; Matsuda, A. BioMed. Chem. Lett. 1994, 4, 721. (f) Takenuki, K.; Itoh, H.; Matsuda, A.; Ueda, T. Chem. Pharm. Bull. 1990, 38, 2947.
28. For examples on the α-facial selective addition of carbon nucleophiles to 2′-keto-pyrimidine nucleosides see: (a) Matsuda, A.; Itoh, H.; Takenuki, K.; Sasaki, T.; Ueda, T. Chem. Pharm. Bull. 1988, 36, 945. (b) Awano, H.; Shuto, S.; Baba, M.; Kira, T.; Shigeta, S.; Matsuda, A. BioMed. Chem. Lett. 1994, 4, 367. (c) Iino, T.; Yoshimura, Y.; Matsuda, A. Tetrahedron 1994, 50, 10397. (d) Ueda, T.; Shuto, S.; Inoue, H. Nucleosides Nucleotides 1984, 3, 173. (e) Yoshimura, Y.; Saitoh, K.; Ashida, N.; Sakata, S.; Matsuda, A. BioMed. Chem. Lett. 1994, 4, 721. (f) Takenuki, K.; Itoh, H.; Matsuda, A.; Ueda, T. Chem. Pharm. Bull. 1990, 38, 2947.
29. For examples on the α-facial selective addition of carbon nucleophiles to 2′-keto-pyrimidine nucleosides see: (a) Matsuda, A.; Itoh, H.; Takenuki, K.; Sasaki, T.; Ueda, T. Chem. Pharm. Bull. 1988, 36, 945. (b) Awano, H.; Shuto, S.; Baba, M.; Kira, T.; Shigeta, S.; Matsuda, A. BioMed. Chem. Lett. 1994, 4, 367. (c) Iino, T.; Yoshimura, Y.; Matsuda, A. Tetrahedron 1994, 50, 10397. (d) Ueda, T.; Shuto, S.; Inoue, H. Nucleosides Nucleotides 1984, 3, 173. (e) Yoshimura, Y.; Saitoh, K.; Ashida, N.; Sakata, S.; Matsuda, A. BioMed. Chem. Lett. 1994, 4, 721. (f) Takenuki, K.; Itoh, H.; Matsuda, A.; Ueda, T. Chem. Pharm. Bull. 1990, 38, 2947.
30. For examples on the α-facial selective addition of carbon nucleophiles to 2′-keto-pyrimidine nucleosides see: (a) Matsuda, A.; Itoh, H.; Takenuki, K.; Sasaki, T.; Ueda, T. Chem. Pharm. Bull. 1988, 36, 945. (b) Awano, H.; Shuto, S.; Baba, M.; Kira, T.; Shigeta, S.; Matsuda, A. BioMed. Chem. Lett. 1994, 4, 367. (c) Iino, T.; Yoshimura, Y.; Matsuda, A. Tetrahedron 1994, 50, 10397. (d) Ueda, T.; Shuto, S.; Inoue, H. Nucleosides Nucleotides 1984, 3, 173. (e) Yoshimura, Y.; Saitoh, K.; Ashida, N.; Sakata, S.; Matsuda, A. BioMed. Chem. Lett. 1994, 4, 721. (f) Takenuki, K.; Itoh, H.; Matsuda, A.; Ueda, T. Chem. Pharm. Bull. 1990, 38, 2947.
31. For examples on the α-facial selective addition of carbon nucleophiles to 2′-keto-pyrimidine nucleosides see: (a) Matsuda, A.; Itoh, H.; Takenuki, K.; Sasaki, T.; Ueda, T. Chem. Pharm. Bull. 1988, 36, 945. (b) Awano, H.; Shuto, S.; Baba, M.; Kira, T.; Shigeta, S.; Matsuda, A. BioMed. Chem. Lett. 1994, 4, 367. (c) Iino, T.; Yoshimura, Y.; Matsuda, A. Tetrahedron 1994, 50, 10397. (d) Ueda, T.; Shuto, S.; Inoue, H. Nucleosides Nucleotides 1984, 3, 173. (e) Yoshimura, Y.; Saitoh, K.; Ashida, N.; Sakata, S.; Matsuda, A. BioMed. Chem. Lett. 1994, 4, 721. (f) Takenuki, K.; Itoh, H.; Matsuda, A.; Ueda, T. Chem. Pharm. Bull. 1990, 38, 2947.
32. Cicero, D. O.; Neuner, P. J. S.; Franzese, O.; D'Onoirio, C.; Iribarren, A. M. BioMed. Chem. Lett. 1994, 4, 861.
33. Hossain, N.; Garg, N.; Chattopadhyaya, J. Tetrahedron 1993, 49, 10061.
34. 1H NMR and MM2 calculations suggest that both 5 and the 2′-ketouridine derivative 4 have similar 3′-endo-puckering. This implies that the (ethoxycarbonyl)methylene moiety of 5 does not alter the sugar puckering to elevate the steric hindrance at the β-face of the 2′-position.
35. (a) Childs, R. F.; Mulholland, D. L.; Nixon, A. Can. J. Chem. 1982, 60, 801.
36. (b) Childs, R. F.; Mulholland, D. L.; Nixon, A. Ibid. 1982, 60, 809.
37. 4, it is not certain whether this shift is due to an increased electron density on C-1′ or to the dimensional anisotropic effect of the 2-carbonyl group.
38. 13C signals was based on DEPT and HSQC (heteronuclear single quantum coherence) experiments.
39. 2NEt, or 1,1,3,3-tetramethylguanidine was attempted. However, decomposition or recovery of the starting material was observed.
40. 6 could not be measured.
41. For examples of the cooperative coordination to mCPBA see: (a) Johnson, M. R.; Kishi, Y. Tetrahedron Lett. 1979, 4347. (b) Clayden, J.; Collington, E. W.; Egert, E.; McElroy, A. B.; Warran, S. J. Chem. Soc., Perkin Trans. 1 1994, 2801. (c) Kogen, H.; Nishi, T. J. Chem. Soc., Chem. Commun. 1987, 311. (d) Jenmalm, A.; Berts, W.; Luthman, K.; Csöregh, I.; Hacksell, U. J. Org, Chem. 1995, 60, 1026.
42. For examples of the cooperative coordination to mCPBA see: (a) Johnson, M. R.; Kishi, Y. Tetrahedron Lett. 1979, 4347. (b) Clayden, J.; Collington, E. W.; Egert, E.; McElroy, A. B.; Warran, S. J. Chem. Soc., Perkin Trans. 1 1994, 2801. (c) Kogen, H.; Nishi, T. J. Chem. Soc., Chem. Commun. 1987, 311. (d) Jenmalm, A.; Berts, W.; Luthman, K.; Csöregh, I.; Hacksell, U. J. Org, Chem. 1995, 60, 1026.
43. For examples of the cooperative coordination to mCPBA see: (a) Johnson, M. R.; Kishi, Y. Tetrahedron Lett. 1979, 4347. (b) Clayden, J.; Collington, E. W.; Egert, E.; McElroy, A. B.; Warran, S. J. Chem. Soc., Perkin Trans. 1 1994, 2801. (c) Kogen, H.; Nishi, T. J. Chem. Soc., Chem. Commun. 1987, 311. (d) Jenmalm, A.; Berts, W.; Luthman, K.; Csöregh, I.; Hacksell, U. J. Org, Chem. 1995, 60, 1026.
44. For examples of the cooperative coordination to mCPBA see: (a) Johnson, M. R.; Kishi, Y. Tetrahedron Lett. 1979, 4347. (b) Clayden, J.; Collington, E. W.; Egert, E.; McElroy, A. B.; Warran, S. J. Chem. Soc., Perkin Trans. 1 1994, 2801. (c) Kogen, H.; Nishi, T. J. Chem. Soc., Chem. Commun. 1987, 311. (d) Jenmalm, A.; Berts, W.; Luthman, K.; Csöregh, I.; Hacksell, U. J. Org, Chem. 1995, 60, 1026.
45. Azuma, A.; Nakajima, Y.; Nishizono, N.; Minakawa, N.; Suzuki, M.; Hanaoka, K.; Kobayashi, T.; Tanaka, M.; Sasaki, T.; Matsuda, A. J. Med. Chem. 1993, 36, 4183.
46. Basu, M. K.; Sarkar, D. C.; Ranu, B. C. Synth. Commun. 1989, 19, 627.