Selective acceleration for deprotection of benzyl ethers with ti-HMS

Tetrahedron Letters

Volumn 39, Issue 51, 1998, Pages 9461-9464

  Itoh, Akichika ^a   Kodama, Tomohiro ^a   Maeda, Shiro ^b   Masaki, Yukio ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^b UNIVERSITY OF FUKUI   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; ETHER DERIVATIVE; PALLADIUM; SILANE DERIVATIVE; SILICON DIOXIDE;

ARTICLE; CATALYST; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTECTION; X RAY POWDER DIFFRACTION;

EID: 0032542191     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02145-5     Document Type: Article

References (21)

1. 1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd Edn., Wiley, N. Y., 1991, pp 47.
2. 2. Tanev, P. T.; Pinnavaia, T. J. Science 1995, 267, 865.
3. 3. 10%Ti-HMS was prepared according to the literatures: Zhang, W.; Froba, M.; Wang, J.; Tanev, P. T.; Wong, J.; Pinnavaia, T. J. J. Am. Chem. Soc. 1996, 118, 9164. Tanev, P. T.; Chibwe, M.; Pinnavaia, T. J. Nature 1994, 368, 321.
4. 3. 10%Ti-HMS was prepared according to the literatures: Zhang, W.; Froba, M.; Wang, J.; Tanev, P. T.; Wong, J.; Pinnavaia, T. J. J. Am. Chem. Soc. 1996, 118, 9164. Tanev, P. T.; Chibwe, M.; Pinnavaia, T. J. Nature 1994, 368, 321.
5. 2-filled balloon was fitted to the flask and the mixture stirred for the times indicated. After filtration through celite or membrane filter, the reaction mixture was concentrated and purified by silicagel column chromatography or preparative TLC.
6. 5. Ward J. W. J. Catal. 1970, 16, 386. Idem. ibid. 1967, 9, 396. Idem. ibid. 1967, 9, 225. Parry, J. B. J. Phys. Chem. 1965, 69, 231.
7. 5. Ward J. W. J. Catal. 1970, 16, 386. Idem. ibid. 1967, 9, 396. Idem. ibid. 1967, 9, 225. Parry, J. B. J. Phys. Chem. 1965, 69, 231.
8. 5. Ward J. W. J. Catal. 1970, 16, 386. Idem. ibid. 1967, 9, 396. Idem. ibid. 1967, 9, 225. Parry, J. B. J. Phys. Chem. 1965, 69, 231.
9. 5. Ward J. W. J. Catal. 1970, 16, 386. Idem. ibid. 1967, 9, 396. Idem. ibid. 1967, 9, 225. Parry, J. B. J. Phys. Chem. 1965, 69, 231.
10. 3 and extracted with ether. The extract was dried, concentrated, and purified by the usual manner.
11. 7. 230-400 mesh of Silicagel 60 (Merck) was used.
12. 8. Some silyl ethers are susceptible to hydrogenolysis: Toshima, K.; Yanagawa, K.; Mukaiyama, S.; Tatsuta, K. Tetrahedron Lett. 1990, 46, 6697. Rao, V. S.; Perlin, A. S. Carbohydr. Res. 1980, 83, 175. Hanessian, S.; Lavallee, P. Can. J. Chem. 1975, 53, 2975. Dodd, G. H.; Golding, B. T.; Ioannou, P. V. J. Chem. Soc., Chem. Commun. 1975, 249. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
13. 8. Some silyl ethers are susceptible to hydrogenolysis: Toshima, K.; Yanagawa, K.; Mukaiyama, S.; Tatsuta, K. Tetrahedron Lett. 1990, 46, 6697. Rao, V. S.; Perlin, A. S. Carbohydr. Res. 1980, 83, 175. Hanessian, S.; Lavallee, P. Can. J. Chem. 1975, 53, 2975. Dodd, G. H.; Golding, B. T.; Ioannou, P. V. J. Chem. Soc., Chem. Commun. 1975, 249. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
14. 8. Some silyl ethers are susceptible to hydrogenolysis: Toshima, K.; Yanagawa, K.; Mukaiyama, S.; Tatsuta, K. Tetrahedron Lett. 1990, 46, 6697. Rao, V. S.; Perlin, A. S. Carbohydr. Res. 1980, 83, 175. Hanessian, S.; Lavallee, P. Can. J. Chem. 1975, 53, 2975. Dodd, G. H.; Golding, B. T.; Ioannou, P. V. J. Chem. Soc., Chem. Commun. 1975, 249. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
15. 8. Some silyl ethers are susceptible to hydrogenolysis: Toshima, K.; Yanagawa, K.; Mukaiyama, S.; Tatsuta, K. Tetrahedron Lett. 1990, 46, 6697. Rao, V. S.; Perlin, A. S. Carbohydr. Res. 1980, 83, 175. Hanessian, S.; Lavallee, P. Can. J. Chem. 1975, 53, 2975. Dodd, G. H.; Golding, B. T.; Ioannou, P. V. J. Chem. Soc., Chem. Commun. 1975, 249. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
16. 8. Some silyl ethers are susceptible to hydrogenolysis: Toshima, K.; Yanagawa, K.; Mukaiyama, S.; Tatsuta, K. Tetrahedron Lett. 1990, 46, 6697. Rao, V. S.; Perlin, A. S. Carbohydr. Res. 1980, 83, 175. Hanessian, S.; Lavallee, P. Can. J. Chem. 1975, 53, 2975. Dodd, G. H.; Golding, B. T.; Ioannou, P. V. J. Chem. Soc., Chem. Commun. 1975, 249. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
17. 4 by the deconvolution analysis is 4.6 : 25.0 : 70.4 for 10% Ti-HMS, and 4.4 : 26.9 : 68.7 for HMS. Thomas, J. M.; Klinowski, J. Advances in Catalysis 1985, 33, 224. Mudrakovskii, I. L.; Mastikhin, U. M.; Shmachkova, V. P.; Kotsarenko, N. S. Chem. Phys. Lett. 1985, 120, 424. Kirkpatrick, R J.; Smith, K. A.; Schramm, S.; Turner, G.; Yang, W. H.Ann. Rev. Earth. Planet Sci. 1985, 13, 29. Klinowski, J.; Thomas, J. M.; Fyfe, C. A.; Gobbi, G. C.; Hartman, J. S. Inorg. Chem. 1983, 22, 63.
18. 4 by the deconvolution analysis is 4.6 : 25.0 : 70.4 for 10% Ti-HMS, and 4.4 : 26.9 : 68.7 for HMS. Thomas, J. M.; Klinowski, J. Advances in Catalysis 1985, 33, 224. Mudrakovskii, I. L.; Mastikhin, U. M.; Shmachkova, V. P.; Kotsarenko, N. S. Chem. Phys. Lett. 1985, 120, 424. Kirkpatrick, R J.; Smith, K. A.; Schramm, S.; Turner, G.; Yang, W. H.Ann. Rev. Earth. Planet Sci. 1985, 13, 29. Klinowski, J.; Thomas, J. M.; Fyfe, C. A.; Gobbi, G. C.; Hartman, J. S. Inorg. Chem. 1983, 22, 63.
19. 4 by the deconvolution analysis is 4.6 : 25.0 : 70.4 for 10% Ti-HMS, and 4.4 : 26.9 : 68.7 for HMS. Thomas, J. M.; Klinowski, J. Advances in Catalysis 1985, 33, 224. Mudrakovskii, I. L.; Mastikhin, U. M.; Shmachkova, V. P.; Kotsarenko, N. S. Chem. Phys. Lett. 1985, 120, 424. Kirkpatrick, R J.; Smith, K. A.; Schramm, S.; Turner, G.; Yang, W. H.Ann. Rev. Earth. Planet Sci. 1985, 13, 29. Klinowski, J.; Thomas, J. M.; Fyfe, C. A.; Gobbi, G. C.; Hartman, J. S. Inorg. Chem. 1983, 22, 63.
20. 4 by the deconvolution analysis is 4.6 : 25.0 : 70.4 for 10% Ti-HMS, and 4.4 : 26.9 : 68.7 for HMS. Thomas, J. M.; Klinowski, J. Advances in Catalysis 1985, 33, 224. Mudrakovskii, I. L.; Mastikhin, U. M.; Shmachkova, V. P.; Kotsarenko, N. S. Chem. Phys. Lett. 1985, 120, 424. Kirkpatrick, R J.; Smith, K. A.; Schramm, S.; Turner, G.; Yang, W. H.Ann. Rev. Earth. Planet Sci. 1985, 13, 29. Klinowski, J.; Thomas, J. M.; Fyfe, C. A.; Gobbi, G. C.; Hartman, J. S. Inorg. Chem. 1983, 22, 63.
21. 11. The XRD patterns were measured on a Rigaku RINT-2000 diffractometer equipped with CuKα radiation (λ= 1.542 A). The diffraction data were collected by using a continuous scan mode with a scan speed of 0.5 deg (2θ)/min.