A novel protecting group for hindered phenols

Tetrahedron Letters

Volumn 39, Issue 18, 1998, Pages 2705-2706

  Hansen, Marvin M ^a   Riggs, Jennifer R ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOL DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ORGANIC CHEMISTRY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0032580326     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00411-0     Document Type: Article

References (9)

1. 1 A Lilly Research Laboratories Summer Internship for J. R. R. is gratefully acknowledged.
2. 2 Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd Ed., Wiley: New York, 1991, pp. 145-174.
3. 3 Trimethylsilyl: Friedman, S.; Kaufman, M. L.; Wender, I. J. Org. Chem. 1962, 27, 664-666. MOM: Introduced under mild conditions but could not be removed under acidic conditions without decomposition of phenol. Hansen, M.M., unpublished results.
4. 4 Hansen, M. M.; Harkness, A. R.; Coffey, D. S.; Bordwell, F. G.; Zhao, Y. Tetrahedron Lett. 1995, 36, 8949-8952.
5. 2O have been used to convert di-tert-butylphenol to the Boc protected derivative in 7% yield, see: Houlihan, F.; Bouchard, F.; Frechet, J. M. J.; Willson, C. G. Can. J. Chem. 1985, 63, 153-162.
6. 6 Prepared as described, see: Hansen, M. M.; Harkness, A. R. Tetrahedron Lett. 1994, 38, 6971-6974.
7. 3, see: Tashiro, M.; Fukata, G. J. Org. Chem. 1977, 42, 1208.
8. 8 See ref 2 pp. 327-329.
9. 4 in dioxane eliminated tert-butylation of tryptophan during peptide Boc cleavage, see: Houghten, R. A.; Beckman, A.; Ostresh, J. M Int. J. Peptide Protein Res. 1986, 27, 653-658.