Mild, selective deprotection of thioacetates using sodium thiomethoxide

Tetrahedron Letters

Volumn 39, Issue 18, 1998, Pages 2693-2694

  Wallace, Owen B ^a   Springer, Dane M ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

THIOACETIC ACID;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS;

EID: 0032580392     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00421-3     Document Type: Article

References (11)

1. 1 Protective Groups in Organic Synthesis, Greene, T.W.; Wuts, P.G.M. Eds. John Wiley & Sons, Inc.: New York, 1991.
2. 2 See, for example: a) Chapman, J.H.; Owen, L.N. J. Chem. Soc. 1950, 579.
3. b) Baddiley, J.; Jamieson, G.A. J. Chem. Soc. 1955, 1085.
4. c) Bobbio, P.A. J. Org. Chem. 1961, 26, 3023.
5. d) Endo, T.; Oda, K., Mukaiyama, T. Chem. Lett. 1974, 443.
6. e) Bianchi, D.; Cesti, P. J. Org. Chem. 1990, 55, 5657
7. f) Choi, J.; Yoon, N.M. Synth. Commun. 1995, 25, 2655.
8. 3 Itokawa, H.; Kondo, K.; Hitotsuyanagi, Y.; Takeya, K. Heterocycles 1993, 56, 1837.
9. 4 All compounds were characterised by NMR spectroscopy and MS or combustion analysis.
10. 5 Treatment of this substrate with ammonia resulted in significant disulfide formation.
11. 6 A similar reaction has been recently carried out using cysteamine as an acetyl transfer agent. Defaye, J ; Guillot, J.-M. Carbohydr. Res. 1994, 253, 185.