Solution and solid phase p-alkoxybenzylation of alcohols under neutral conditions

Tetrahedron Letters

Volumn 40, Issue 4, 1999, Pages 671-674

  Hanessian, Stephen ^a   Huynh, Hoan Khai ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

P Methoxybenzyl (JAMB) ether; Pyridylthiocarbonate; Solid phase alkylation

Indexed keywords

4 METHOXYBENZYL 2 PYRIDYLTHIOCARBONIC ACID; 4 METHOXYBENZYL ETHER; ALCOHOL; UNCLASSIFIED DRUG;

ALCOHOL METABOLISM; ARTICLE; CHEMICAL REACTION KINETICS; ORGANIC CHEMISTRY; REACTION TIME; SPECTROSCOPY; STRUCTURE ANALYSIS;

EID: 0033593561     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02531-3     Document Type: Article

References (21)

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9. For the utilization of 2-pyridylthiocarbonate as an activating group in glycoside synthesis, see B. Lou.; Huynh, H.K.; Hanessian, S. in Preparative Carbohydrate Chemistry, Hanessian, S. Ed., Chapter 19, p. 431 (1996), Dekker, New York; Hanessian, S.; Reddy, G.V.; Huynh, H.K.; Pan, J.; Pedatella, S. Bioorg. Med. Chem. Lett. 1997, 7, 2729. For other applications, see Corey, E. J.; Clark, D. A. Tetrahedron Lett. 1979, 2875; Gosh, A.K.; Duong, T.T.; McKee, S. P. Tetrahedron Lett., 1991, 32 4251.
10. For the utilization of 2-pyridylthiocarbonate as an activating group in glycoside synthesis, see B. Lou.; Huynh, H.K.; Hanessian, S. in Preparative Carbohydrate Chemistry, Hanessian, S. Ed., Chapter 19, p. 431 (1996), Dekker, New York; Hanessian, S.; Reddy, G.V.; Huynh, H.K.; Pan, J.; Pedatella, S. Bioorg. Med. Chem. Lett. 1997, 7, 2729. For other applications, see Corey, E. J.; Clark, D. A. Tetrahedron Lett. 1979, 2875; Gosh, A.K.; Duong, T.T.; McKee, S. P. Tetrahedron Lett., 1991, 32 4251.
11. For the utilization of 2-pyridylthiocarbonate as an activating group in glycoside synthesis, see B. Lou.; Huynh, H.K.; Hanessian, S. in Preparative Carbohydrate Chemistry, Hanessian, S. Ed., Chapter 19, p. 431 (1996), Dekker, New York; Hanessian, S.; Reddy, G.V.; Huynh, H.K.; Pan, J.; Pedatella, S. Bioorg. Med. Chem. Lett. 1997, 7, 2729. For other applications, see Corey, E. J.; Clark, D. A. Tetrahedron Lett. 1979, 2875; Gosh, A.K.; Duong, T.T.; McKee, S. P. Tetrahedron Lett., 1991, 32 4251.
12. For the utilization of 2-pyridylthiocarbonate as an activating group in glycoside synthesis, see B. Lou.; Huynh, H.K.; Hanessian, S. in Preparative Carbohydrate Chemistry, Hanessian, S. Ed., Chapter 19, p. 431 (1996), Dekker, New York; Hanessian, S.; Reddy, G.V.; Huynh, H.K.; Pan, J.; Pedatella, S. Bioorg. Med. Chem. Lett. 1997, 7, 2729. For other applications, see Corey, E. J.; Clark, D. A. Tetrahedron Lett. 1979, 2875; Gosh, A.K.; Duong, T.T.; McKee, S. P. Tetrahedron Lett., 1991, 32 4251.
13. For an example of solid phase p-alkoxybenzylation under Lewis acidic conditions, see Hanessian, S.; Xie, F. Tetrahedron Lett. 1998, 39, 733
14. a. For examples of O-alkylation on solid phase, see: Moon, H.-S.; Schore, N. E.; Kurth, M.J. Tetrahedron Lett. 1994, 35, 8915; also, Crowly, T. I.; Rapoport, H. Acc. Chem. Res. 1976, 9, 135 and the references cited therein;
15. a. For examples of O-alkylation on solid phase, see: Moon, H.-S.; Schore, N. E.; Kurth, M.J. Tetrahedron Lett. 1994, 35, 8915; also, Crowly, T. I.; Rapoport, H. Acc. Chem. Res. 1976, 9, 135 and the references cited therein;
16. b. For polymer-bound tritylation using trityl chloride resin, see for an example: Chan, C.; Randall, L. A. A.; Miller, R. B.; Jones, A. D.; Kurth, M. T. J. Am. Chem. Soc., 1994, 116, 2661; also Fyles, T. M.; Leznoff, C. C. Can. J. Chem. 1976, 54, 435;
17. b. For polymer-boundtritylation using trityl chloride resin, see for an example: Chan, C.; Randall, L. A. A.; Miller, R. B.; Jones, A. D.; Kurth, M. T. J. Am. Chem. Soc., 1994, 116, 2661; also Fyles, T. M.; Leznoff, C. C. Can. J. Chem. 1976, 54, 435;
18. c. For Mitsunobu attachment of phenols on Wang resin, see: Richter, L.; Cradek, T. R. Tetrahedron Lett. 1994, 35, 4705;
19. d. For polymer-bound THP ethers using DHP resin, see: Thompson, L. A.; Ellman, J. A. Tetrahedron Lett. 1994, 35, 9333.
20. 2, then dried. IR analysis showed the absence of hydroxyl peaks. The TOPCAT resin could be stored as a dry powder at 0° without change.
21. For diversely substituted benzyl ethers and their cleavage, see, Gaunt, M. J.; Yu, J.; Spencer, J. B. J. Org. Chem. 1998, 63, 4172.