Chemoselective inhibition of the hydrogenolysis of the MPM protective group for phenolic hydroxy functions using a Pd/C-pyridine catalyst

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 399-402

  Sajiki, Hironao ^a   Kuno, Hiroko ^a   Hirota, Kosaku ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HYDROGENATION; IN VITRO STUDY; METHODOLOGY;

EID: 0031022264     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02309-X     Document Type: Article

References (17)

1. (a) Green, T. W.; Wuts, P. G. Protective Groups in Organic Synthesis; Wiley-Interscience: New York, 2nd ed., 1991; pp. 47-53 and 156-158.
2. (b) Rylander, P. N. Hydrogenation Methods; Academic Press: New York, 1985; pp. 157-163.
3. (c) Idem. Catalytic Hydrogenation in Organic Synthesis; Academic Press: New York, 1979, pp. 271-279.
4. (d) Freifelder, M. Practical Catalytic Hydrogenation Techniques and Applications; Wiley-Interscience: New York, 1971, pp. 398-413 and 428-440.
5. Sajiki, H. Tetrahedron Lett. 1995, 36, 3465.
6. (a) McPhee, W. D.; Erickson, E. S. J. Am. Chem. Soc. 1946, 68, 624.
7. (b) Czech, B. P.; Bartsh, R. A. J. Org. Chem. 1984, 49, 4077.
8. Davis, R.; Muchowski, J. M. Synthesis 1982, 987.
9. Satisfactory analytical data were obtained for all new compounds.
10. Young, S. D.; Tamburini, P. P. J. Am. Chem. Soc. 1989, 111, 1933.
11. Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021 and references cited therein.
12. White, J. D.; Amedio, J. C. J. Org. Chem. 1989, 54, 736.
13. Srikrishna, A.; Viswajanani, R.; Sattigeri, J. A.; Vijaykumar, D. J. Org. Chem. 1995, 60, 5961.
14. 4 soln. (not for product 11) and water and evaporated to give a product. The product was purified with silica gel column chromatography if necessary.
15. 2 the smooth cleavage of O-benzyl protection of Boc-Tyr(Bn)-OH under the hydrogenolysis condition with a Pd/C-ammonia system (30 min, 89 %).
16. Under the hydrogenolysis condition without pyridine, reasonably selective removal of the Cbz protecting group of 6 was also observed due to the effect of the amino group of the product 7.
17. 7 that the selective removal of an aliphatic O-benzyl protection in the presence of a MPM protective group for aliphatic hydroxy functions was achieved with hydrogenolysis over W-4 Raney nickel, although a large excess amount of catalyst was required to complete the reaction.