Ytterbium(III) triflate-catalyzed selective methanolysis of methoxyacetates: A new deprotective method

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4491-4492

  Hanamoto, Takeshi ^a   Sugimoto, Yuichi ^a   Yokoyama, Yasuo ^a   Inanaga, Junji ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001755181     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960095g     Document Type: Article

References (22)

1. Reese, C. B.; Stewart, J. C. M. Tetrahedron Lett. 1968, 4273-4276.
2. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; John Wiley and Sons: New York, 1991; pp 10-142.
3. (a) Thom, K. F. U.S. Patent 3615169, 1971; Chem. Abstr. 1972, 76, 5436a.
4. (b) Almasio, M. C.; Arnaud-Neu, F.; Schwing-Weill, M. J. Helv. Chim. Acta 1983, 66, 1296-1306.
5. (c) Forsberg, J. H.; Spaziano, V. T.; Balasubramanian, T. M.; Liu, G. K.; Kinsley, S. A.; Duckworth, C. A.; Poteruca, J. J.; Brown, P. S.; Miller, J. L. J. Org. Chem. 1987, 52, 1017-1021.
6. 3.
7. For the lanthanide(III) triflate-catalyzed glycosylation of 1-O-methoxyacetyl sugars, see: Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791-2794. See also: Inanaga, J.; Yokoyama, Y.; Hanamoto, T. J. Chem. Soc., Chem. Commun. 1993, 1090-1091.
8. For the lanthanide(III) triflate-catalyzed glycosylation of 1-O-methoxyacetyl sugars, see: Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791-2794. See also: Inanaga, J.; Yokoyama, Y.; Hanamoto, T. J. Chem. Soc., Chem. Commun. 1993, 1090-1091.
9. For a MNDO-PM3 study on the selective activation of 1-methoxyacetyl sugars by zinc(II) ion, see: Inanaga, J.; Yokoyama, Y.; Sugimoto, Y.; Hanamoto, T. Mem. Fac. Sci., Kyushu Univ. Ser. C, Chem. 1993, 19, 29-32.
10. 3-catalyzed reactions, see: (a) Hosono, S.; Kim, W.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 4-5. (b) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423-424. (c) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413-4414. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227-2232. (e) Kobayashi, S. Synlett. 1994, 689-701. (f) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639-4640. (g) Matsubara, S.; Yoshioka, M.; Utimoto, K. Chem. Lett. 1994, 827-830. (h) Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433-436. (i) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601.
11. 3-catalyzed reactions, see: (a) Hosono, S.; Kim, W.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 4-5. (b) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423-424. (c) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413-4414. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227-2232. (e) Kobayashi, S. Synlett. 1994, 689-701. (f) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639-4640. (g) Matsubara, S.; Yoshioka, M.; Utimoto, K. Chem. Lett. 1994, 827-830. (h) Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433-436. (i) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601.
12. 3-catalyzed reactions, see: (a) Hosono, S.; Kim, W.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 4-5. (b) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423-424. (c) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413-4414. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227-2232. (e) Kobayashi, S. Synlett. 1994, 689-701. (f) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639-4640. (g) Matsubara, S.; Yoshioka, M.; Utimoto, K. Chem. Lett. 1994, 827-830. (h) Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433-436. (i) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601.
13. 3-catalyzed reactions, see: (a) Hosono, S.; Kim, W.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 4-5. (b) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423-424. (c) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413-4414. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227-2232. (e) Kobayashi, S. Synlett. 1994, 689-701. (f) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639-4640. (g) Matsubara, S.; Yoshioka, M.; Utimoto, K. Chem. Lett. 1994, 827-830. (h) Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433-436. (i) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601.
14. 3-catalyzed reactions, see: (a) Hosono, S.; Kim, W.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 4-5. (b) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423-424. (c) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413-4414. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227-2232. (e) Kobayashi, S. Synlett. 1994, 689-701. (f) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639-4640. (g) Matsubara, S.; Yoshioka, M.; Utimoto, K. Chem. Lett. 1994, 827-830. (h) Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433-436. (i) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601.
15. 3-catalyzed reactions, see: (a) Hosono, S.; Kim, W.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 4-5. (b) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423-424. (c) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413-4414. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227-2232. (e) Kobayashi, S. Synlett. 1994, 689-701. (f) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639-4640. (g) Matsubara, S.; Yoshioka, M.; Utimoto, K. Chem. Lett. 1994, 827-830. (h) Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433-436. (i) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601.
16. 3-catalyzed reactions, see: (a) Hosono, S.; Kim, W.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 4-5. (b) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423-424. (c) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413-4414. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227-2232. (e) Kobayashi, S. Synlett. 1994, 689-701. (f) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639-4640. (g) Matsubara, S.; Yoshioka, M.; Utimoto, K. Chem. Lett. 1994, 827-830. (h) Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433-436. (i) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601.
17. 3-catalyzed reactions, see: (a) Hosono, S.; Kim, W.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 4-5. (b) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423-424. (c) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413-4414. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227-2232. (e) Kobayashi, S. Synlett. 1994, 689-701. (f) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639-4640. (g) Matsubara, S.; Yoshioka, M.; Utimoto, K. Chem. Lett. 1994, 827-830. (h) Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433-436. (i) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601.
18. 3-catalyzed reactions, see: (a) Hosono, S.; Kim, W.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 4-5. (b) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423-424. (c) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413-4414. (d) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227-2232. (e) Kobayashi, S. Synlett. 1994, 689-701. (f) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639-4640. (g) Matsubara, S.; Yoshioka, M.; Utimoto, K. Chem. Lett. 1994, 827-830. (h) Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433-436. (i) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601.
19. 3 (99%).
20. 3, catalyzed acylation of alcohols, see ref 7c.
21. For example, the methanolysis of benzyl methoxyacetate with the recovered catalyst under the same conditions afforded benzyl alcohol in 91% isolated yield.
22. Prepared from 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose and methoxyacetyl chloride according to the standard esterification procedure.