Removal of acetal, silyl, and 4, 4′-dimethoxytrityl protecting groups from hydroxyl functions of carbohydrates and nucleosides with clay in aqueous methanol

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 9026-9027

  Asakura, Jun Ichi ^a,b   Robins, Morris J ^a   Asaka, Yukihiro ^a   Kirn, Tong Hei ^a  

^a KINKI UNIVERSITY SCHOOL OF MEDICINE   (Japan)

^b Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000903679     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961376r     Document Type: Article

References (33)

1. (a) De Beider, A. N. Adv. Carbohydr. Chem. Biochem. 1977, 34, 179.
2. (b) Clode, D. M. Chem. Rev. 1979, 79, 491.
3. Lalonde, M.; Chan, T. H. Synthesis 1985, 817.
4. Greene, T. W.; Wuts, P. G. M. In Protective Groups in Organic Synthesis, 2nd ed.; John Wiley & Sons: New York, 1991; pp 53-86, 119-142 and references therein.
5. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
6. (a) Shekhani, M. S.; Khan, K. M.; Mahmood, K. Tetrahedron Lett. 1988, 29, 6161.
7. (b) Monger, S. J.; Parry, D. M.; Roberts, S. M. J. Chem. Soc., Chem. Commun. 1989, 381.
8. Cormier, J. F. Tetrahedron Lett. 1991, 32, 187.
9. Zhang, W.; Robins, M. J. Tetrahedron Lett. 1992, 33, 1177 and references therein.
10. (a) Hoyer, S.; Laszlo, P. Synthesis 1986, 655.
11. (b) Kawai, M.; Onaka, M.; Izumi, Y. Bull. Chem. Soc. Jpn. 1988, 61, 2157.
12. Labiad, B.; Villemin, D. Synthesis 1989, 143.
13. Labiad, B.; Villemin, D. Synth. Commun. 1989, 19, 31.
14. (e) Higuchi, K.; Onaka, M.; Izumi, Y. J. Chem. Soc., Chem. Commun. 1991, 1035.
15. (f) Tsujimoto, M.; Matsubara, Y.; Yoshihara, M.; Maeshima, T.; Asakura, J. Chem. Express 1991, 6, 825.
16. (g) Onaka, M.; Shinoda, T.; Izumi, Y.; Nolen, E. Chem. Lett. 1993, 117.
17. (h) Fukase, K.; Winarno, H.; Kusumoto, S. Chem. Express 1993, 8, 409.
18. Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141.
19. (j) Tateiwa, J.; Horiuchi, H.; Uemura, S. J. Org. Chem. 1995, 60, 4039 and references therein.
20. Asakura, J.; Matsubara, Y.; Yoshihara, M. J. Carbohydr. Chem. 1996, 15, 231.
21. Asakura, J.; Tomura, T. Nucleosides Nucleotides 1988, 7, 245.
22. Asakura, J. Nucleosides Nucleotides 1993, 12, 701.
23. Cunico, R. F.; Bedell, L. J. Org. Chem. 1980, 45, 4797.
24. In the case of 13, elevated reaction temperatures and/or longer reaction times resulted in increased formation of byproducts (TLC).
25. Fromageot, H. P. M.; Griffin, B. E.; Reese, C. B.; Sulston, J. E. Tetrahedron 1967, 23, 2315.
26. Nair, V.; Buenger, G. S. Org. Prep. Proc. Int. 1990, 22, 57.
27. (a) Markiewicz, W. T. J. J. Chem. Res. (S) 1979, 24.
28. (b) Robins, M. J.; Wilson, J. S.; Hansske, F. J. Am. Chem. Soc. 1983, 705, 4059.
29. Ogilvie, K. K.; Thompson, E. A.; Quilliam, M. A.; Westmore, J. B. Tetrahedron Lett. 1974, 33, 2865.
30. Hanessian, S.; Lavallee, P. Can. J. Chem. 1975, 53, 2975.
31. (a) Smith, M.; Rammler, D. H.; Goldberg, I. H.; Khorana, H. G. J. Am. Chem. Soc. 1962, 84, 430.
32. (b) Hakimelahi, G. H.; Proba, Z. A.; Ogilvie, K. K. Can. J. Chem. 1982, 60, 1106.
33. Robins, M. J.; Mengel, R.; Jones, R. A.; Fouron, Y. J. Am. Chem. Soc. 1976, 98, 8204.