A novel thiol protecting group: A 2-thioquinoline sulfide as a masked sulfhydryl moiety

Tetrahedron Letters

Volumn 40, Issue 8, 1999, Pages 1467-1470

  Zhang, Jiancun ^a   Matteucci, Mark D ^a  

^a GILEAD SCIENCES   (United States)

Author keywords

Protecting group; Quinoline and nucleoside; Thiol

Indexed keywords

2 THIOQUINOLINE SULFIDE; ACETIC ACID; CYANOBOROHYDRIDE SODIUM; QUINOLINE DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; ORGANIC CHEMISTRY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033582711     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02694-X     Document Type: Article

References (12)

1. (a) Green, T. W.; Wuts, P. G. In Protective Groups in Organic Synthesis 2nd Edition; John Wiley & Sons: New York, NY, 1991, p277.
2. (b) Wolman, Y. In Thiol Function Patai, S. Ed.; John Wiley & Sons: London, 1974, p669.
3. (c) Bodansky, M. Peptide Chemistry: A Practical Text Book Springer-Verlag: Berlin, 1988, p89.
4. (a) Jones, R. J., Lin, K.-Y., Milligan, J. F., Wadwani, S.; Matteucci, M. D. J. Org. Chem. 1993, 58, 2893.
5. (b) Zhang, J.; Matteucci, M.D. Tetrahedron Lett., 1995, 36, 8375.
6. (c) Zhang, J., Shaw, J. T.; Matteucci, M.D. Bioorganic & Medicinal Letters, submitted.
7. (a) Gribble, G. W.; Heald, P. W. Synthesis, 1975, 650.
8. (b) Egucji, S., Matsushita, Y. and Takeuchi, H. J. Org. Chem. 1992, 57, 6925.
9. 2-Quinolinethiol is commercially available from Aldrich, and Pfaltz and Bauer.
10. Medina, J. C., Salomon, M.; Kyler, K. S. Tetrahedron Lett. 1988, 29, 3773.
11. 2 to give 3.1 g of thiol 7 in 95% yield.
12. It was sometimes difficult to avoid the formation of a small amount of disulfide during deprotection of thioesters with hydroxides or ammonia because the basic condition accelerated disulfide formation.