(R)-2,3-cyelohexylideneglyeeraldehyde: A potential intermediate for convenient synthesis of 2-C-branched 2-deoxypentofuranoses

Journal of Organic Chemistry

Volumn 64, Issue 18, 1999, Pages 6874-6878

  Chattopadhyay, A ^a   Dhotare, B ^a   Hassarajani, S ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEOXYNUCLEOSIDE DERIVATIVE; GLYCERALDEHYDE; MANNITOL;

CHEMICAL STRUCTURE; ENANTIOMER; ISOMER; NOTE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032886746     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982130k     Document Type: Note

References (67)

1. (a) Bartlett, P. A. Tetrahedron 1980, 36, 3.
2. (b) Eliel, E. L.; Otsuka, S. Asymmetric Reactions and Processes in Chemistry; ACS Symposium Series 185; American Chemical Society: Washington, DC, 1982.
3. (c) Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 181-238.
4. (d) Mulzer, J.; Attenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. Organic Synthesis Highlights; VCH: Weinheim, 1991, pp 1-118.
5. (e) Marshall, J. A. Chem. Rev. 1996, 96, 31.
6. (f) Stephenson, G. R. Advanced Asymmetric Synthesis; Chapman & Hall: New York, 1996.
7. (g) Mukaiyama, T. Org. React. 1982, 28, 103.
8. (h) Yamamoto, Y.; Asaao, N. Chem. Rev. 1993, 93, 2207.
9. (i) Keck, G. E.; Kenneth, A. S.; Cressman, E. N. K.; Abott, D. E. J. Org. Chem. 1994, 59, 7889.
10. (j) Chemler, S. R.; Roush, W. R. J. Org. Chem. 1998, 63, 3800 and references therein.
11. (k) Heathcock, C. H.; Pirrung, M. C.; Montegomery, S. H.; Lampe, J. Tetrahedron 1981, 37, 4095.
12. (l) Dondoni, A.; Orduna, J.; Merino, P. Synthesis 1992, 201.
13. (m) Mulzer, J.; Angermann, A. Tetrahedron Lett. 1983, 24, 2843.
14. (n) Buse, C. T.; Heathcock, C. H. Tetrahedron Lett. 1978, 19, 1685.
15. (o) Corey, E. J.; Yu, C. M.; SooKim, S. J. Am. Chem. Soc. 1989, 111, 5495.
16. (p) Sakurai, H. Synlett 1989, 1 and references therein.
17. (a) Reetz, M. K.; Rotfling, K.; Griebenow, N. Tetrahedron Lett. 1994, 35, 1969.
18. (b) Marco, J. L.; Martin, G.; Marninez-Grau, A.; Cano, F. H. Tetrahedron 1993, 49, 7133.
19. (c) Sjechner, B.; Achmatowich, O.; Caldecki, Z. Tetrahedron 1994, 50, 7611.
20. (a) Li, C. J. Chem. Rev. 1993, 93, 2023.
21. (b) ref 1d, pp 71-76.
22. (c) Li, C. J. Tetrahedron 1996, 52, 5643.
23. (d) Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741.
24. Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon Press Ltd.: New York, 1986; and references therein.
25. (b) Mori, K. Total Synthesis of Natural Products; Apsimon, J., Ed.; John Wiley & Sons: New York, 1992; Vol. 9 and references therein.
26. (c) Hanessian, S. Pure Appl. Chem. 1993, 65, 1189.
27. (a) Chattopadhyay, A.; Mamdapur, V. R. J. Org. Chem. 1995, 60, 585.
28. (b) Chattopadhyay, A. J. Org. Chem. 1996, 61, 6104.
29. (a) Petrier, C.; Luche, J. L. J. Org. Chem. 1986, 50, 910.
30. (b) Einhorn, C.; Luche, J. L. J. Organomet. Chem. 1987, 322, 177.
31. Roush, W. R.; Adams, M. A.; Walts, A. E.; Harries, D. J. J. Am. Chem. Soc. 1986, 108, 3422.
32. (a) Anh, N. T. Topp. Cur. Chem. 1980, 58, 145.
33. (b) Cherest, M.; Felkin, H. Tetrahedron Lett. 1968, 9, 2205.
34. Hayashi, T.; Kabeta, K.; Hamachi, I.; Kumuda, M. Tetrahedron Lett. 1983, 24, 2865.
35. Hoffman, R. W.; Zeiss, H. J. J. Org. Chem. 1981, 46, 1309.
36. (a) Dueholm, K. L.; Pedersen, E. B. Synthesis 1992, 1 and references therein.
37. (b) Hury, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745 and references therein.
38. (c) Lipshutz, B. H.; Hayawaka, H.; Kato, K.; Lowe, R. F. Synthesis 1994, 1476 and references therein.
39. (d) Wilson, L. J.; Hager, M. W.; El-Kattan, Y. A.; Liotta, D. C. Synthesis 1995, 1465 and references therein.
40. (e) Ait-Sir, H.; Fahmi, N.; Goenthal, G.; Ronco, G.; Tber, B.; Villa, P.; Ewing, D.; Mackemzie, G. J. Chem. Soc., Perkin Trans. 1 1996, 1667.
41. (f) Raifeld, Y. E.; Nikitenko, A. A.; Arshava, B. M.; Mikerin, I. E.; Zilburg, L. L.; Ya. Vid, G.; Lang, S. A.; Lee, V. J. Tetrahedron 1994, 50, 8603.
42. (a) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Minakawa, N.; Matsuda, A. J. Org. Chem. 1998, 63, 746 and references therein.
43. (b) Harry-O'kuru, R. E.; Smith, J. M.; Wolfe, M. S. J. Org. Chem. 1997, 62, 1754 and references therein.
44. (a) Hossain, N.; Blaton, N.; Peeters, O.; Rozenski, J.; Herdewijn, P. A. Tetrahedron 1996, 38, 5563.
45. (b) Goodman, B. K; Greenberg, M. M. J. Org. Chem. 1996, 61, 1754.
46. (c) Ono, A.; Dan, A.; Matsuda, A. Bioconjugate Chem. 1993, 4, 499.
47. (d) Yoshimura, Y.; Otter, B. A.; Ueda, T.; Matsuda, A. Chem. Pharm. Bull. 1992, 40, 1761.
48. (a) Yoshimura, Y.; Saitoh, K.; Ashida, N.; Sakata, S. Bioorg. Med. Chem. Lett. 1994, 4, 721.
49. (b) Cirero, D. O.; Neuner, P. J.; Franzese, O.; D'Onofrio, C.; Iribarren, A. M. Bioorg. Med. Chem. Lett. 1994, 4, 861.
50. (c) MaCarthy, J. R.; Mathews, D. P.; Stemerick, D. M.; Huber, E. W.; Bey, P.; Lippert, B. J.; Snyder, R. D.; Sunkara, P. S. J. Am. Chem. Soc. 1991, 113, 7439.
51. (d) Samano, V.; Robins, M. J. J. Am. Chem. Soc. 1992, 114, 4007.
52. (a) Svansson, L.; Kvarnstrom, I. J. Org. Chem. 1991, 56, 2993.
53. (b) Johnson, C. R.; Rhumralkar, D.; Clercq, E. Nucleosides Nucleotides 1995, 14, 185.
54. (c) Hossain, N.; Plavec, J.; Chattopadhyay, J. Tetrahedron 1994, 36, 4167.
55. (d) Auguste, S. P.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1995, 395.
56. (a) Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K; Miyasaka, T. J. Org. Chem. 1996, 61, 851.
57. (b) Thrane, H.; Fensholdt, J.; Regner, M.; Wengel, J. Tetrahedron 1995, 37, 10389.
58. Hassan, A. E. A.; Shuto, S.; Matsuda, A. Tetrahedron 1994, 36, 689.
59. Lawrence, A. J.; Pavey, J. B. J.; Cosstick, R. Tetrahedron Lett. 1995, 36, 6341.
60. (a) Sugimura, H.; Osumi, K.; Yamazaki, T.; Yamaya, T. Tetrahedron Lett. 1991, 32, 1809.
61. (b) Sugimura, H.; Osumi, K.; Yamazaki, T.; Yamaya, T. Tetrahedron Lett. 1991, 32, 1813.
62. Hansen, P.; Pedersen, E. B. Acta Chem. Scand. 1990, 44, 522.
63. (a) Xia, X.; Wang, J.; Hager, M. W.; Sisti, N.; Liotta, D. C. Tetrahedron Lett. 1997, 38, 1113.
64. (b) Jung, M. E.; Castro, C. J. Org. Chem. 1993, 58, 807.
65. Grauert, M.; Schollkopf, U. Liebigs Ann. Chem. 1985, 1817.
66. (a) Takano, S.; Akiyama, M.; Sato, S. Ogasawara, K. Chem. Lett. 1983, 1593.
67. (b) Naruta, Y.; Nagai, N.; Maruyama, K. Chem. Lett. 1983, 1383.