Polymer-bound p-alkoxybenzyl trichloracetimidates: Reagents for the protection of alcohols as benzyl ethers on solid-phase

Tetrahedron Letters

Volumn 39, Issue 8, 1998, Pages 733-736

  Hanessian, Stephen ^a   Xie, Fang ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

4 ALKOXYBENZYL TRICHLORACETIMIDATE; ALCOHOL DERIVATIVE; POLYMER; RESIN; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; NONHUMAN; SOLID PHASE EXTRACTION; SUSPENSION;

EID: 0032546147     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10684-0     Document Type: Article

References (27)

1. 1. For recent reviews, see: a. Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17;
2. b. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-54; 1997, 53, 5643..
3. b. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-54; 1997, 53, 5643..
4. 2. For recent reviews, see: a. Balkenhohl, F.; Bussche-Hünnefeld, C. V. D.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288;
5. b. Thompson, L. A.; Ellman, J. Chem. Rev. 1996, 96, 555;
6. c. Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144;
7. d. Ellman, J. A. Acc. Chem. Res. 1996, 29, 132;
8. e. Gordon, E. M. Curr. Opin. Biotechnol. 1995, 6, 624;
9. f. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385;
10. g. Gallop, M. A.; Barett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 57, 1233.
11. 3. a. For polymer-bound benzylation of alkoxides using the Merrifield resin, see for an example: Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915; also, Crowley, J. I.; Rapoport, H. Acc. Chem. Res. 1976, 9, 135 and the references cited therein;
12. 3. a. For polymer-bound benzylation of alkoxides using the Merrifield resin, see for an example: Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915; also, Crowley, J. I.; Rapoport, H. Acc. Chem. Res. 1976, 9, 135 and the references cited therein;
13. b. For polymer-bound tritylation using trityl chloride resin, see for an example: Chen, C.; Randall, L. A. A.; Miller, R. B.; Jones, A. D.; Kurth, M. J. J. Am. Chem. Soc. 1994, 116, 2661; also, Fyles, T. M.; Leznoff, C. C. Can. J. Chem. 1976, 54, 935;
14. b. For polymer-bound tritylation using trityl chloride resin, see for an example: Chen, C.; Randall, L. A. A.; Miller, R. B.; Jones, A. D.; Kurth, M. J. J. Am. Chem. Soc. 1994, 116, 2661; also, Fyles, T. M.; Leznoff, C. C. Can. J. Chem. 1976, 54, 935;
15. c. For Mitusnobu attachment of phenols on Wang resin, see: Richter, L.; Gadek, T. R. Tetrahedron Lett. 1994, 35, 4705;
16. d. For polymer-bound THP ether using DHP resin, see: Thompson, L. A.; Ellman, J. A. Tetrahedron Lett. 1994, 35, 9333.
17. 4. Hanessian, S.; Ogawa, T.; Guindon, Y.; Kamennof, J.; Roy, R. Carbohydr. Res. 1974, 38, C15.
18. 5. Frechet, J. M.; Schuerch, C. J. Am. Chem. Soc. 1971, 93, 492.
19. 6. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5835.
20. 7. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis John Wiley&Sons, Inc.: New York, 1991.
21. 8. Wang, S.-W. J. Am. Chem. Soc. 1973, 95, 1328.
22. 9. a. Bayer, E. Angew. Chem. Int. Ed. Engl. 1991, 30, 113:
23. b. Bayer, E.; Rapp, W. Ger. Offen. DE Pat. 3,500,180, 1986.
24. 10. Iversen, T.; Bundle, K. R. J. Chem. Soc., Chem. Commun. 1981, 1240.
25. 11. a. Nakajima, N.; Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett. 1988, 29, 4139;
26. b. Takaku, H.; Ueda, S.; Ito, T. Tetrahedron Lett. 1983, 24, 5363.
27. 12. For an example of cleavage of p-methoxybenzyl (PMB) ether using TFA in solution, see: Yan, L.; Kahne, D. Synlett 1995, 523.