A convenient and simple procedure for the preparation of nitrate esters from alcohols employing LiNO3/(CF3CO)2O

Tetrahedron Letters

Volumn 46, Issue 37, 2005, Pages 6205-6207

  Gavrila, Adina ^a   Andersen, Lisbeth ^a   Skrydstrup, Troels ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Alcohols; Carbohydrates; Nitrate esters; Peptides; Steroids

Indexed keywords

ACETONITRILE; ACID ANHYDRIDE; ALCOHOL DERIVATIVE; ESTER DERIVATIVE; LITHIUM DERIVATIVE; MONOSACCHARIDE; NITRIC ACID DERIVATIVE; OXYGEN DERIVATIVE; PEPTIDE; STEROID;

AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; NITRATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION;

EID: 23744491386     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.065     Document Type: Article

References (21)

1. R.W. Binkley, and D.J. Koholic J. Org. Chem. 44 1979 2047 2048
2. R.W. Binkley, and D.J. Koholic J. Carbohydr. Chem. 3 1984 85 106
3. T.F. Tam, and B. Fraser-Reid J. Chem. Soc., Chem. Commun. 1984 1122 1123
4. J.C. Lopez, R. Alonso, and B. Fraser-Reid J. Am. Chem. Soc. 111 1989 6471 6473
5. W.A. Yeung, R. Alonso, G.D. Vite, and B. Fraser-Reid J. Carbohydr. Chem. 3 1989 413 427
6. M.J. Begley, R.J. Fletcher, J.A. Murphy, and M.S. Sherburn J. Chem. Soc., Chem. Commun. 1993 1723 1725
7. N. Hussain, D.O. Morgan, C.R. White, and J.A. Murphy Tetrahedron Lett. 35 1994 5069 5072
8. C.G. Francisco, E.I. León, A. Martín, P. Moreno, M.S. Rodrígez, and E. Suárez J. Org. Chem. 66 2001 6967 6976
9. M.J. Robins, Z. Guo, M.C. Samano, and S.F. Wnuk J. Am. Chem. Soc. 121 1999 1425 1433
10. C.J. Easton, A.J. Ivory, and C.A. Smith J. Chem. Soc., Perkin Trans. 2 1997 503 507
11. H.A. Headlam, A. Mortimer, C.J. Easton, and M.J. Davies Chem. Res. Toxicol. 13 2000 1087 1095
12. M. Ricci, L. Madariaga, and T. Skrydstrup Angew. Chem., Int. Ed. 39 2000 242 245
13. M. Ricci, P. Blakskjær, and T. Skrydstrup J. Am. Chem. Soc. 122 2000 12413 12421
14. P. Blakskjær, A. Gavrila, L. Andersen, and T. Skrydstrup Tetrahedron Lett. 45 2004 9091 9094
15. R. Boschan, R.T. Merrow, and R.W. van Dolah Chem. Rev. 55 1955 485 510
16. R.D. Campbell, and F.E. Behr J. Org. Chem. 38 1973 1183 1186
17. R.G. Coombes D.H.R. Barton W.D. Ollis Comprehensive Organic Chemistry: The Synthesis and Reactions of Organic Compounds Vol. 2 1979 Pergamon Press Oxford pp 360-363
18. G.A. Olah, Q. Wang, X. Li, and G.K. Surya Prakash Synthesis 1993 207 208
19. Other two-step procedures are also known such as alcohol to sulfonate transformation followed by substitution with a nitrate salt (Ref. 3), or generation of a chloroformate followed by treatment with silver nitrate (Ref. 18).
20. 2 followed by drying and evaporation under reduced pressure afforded the nitrate ester, which was purified by recrystallization from EtOAc/hexane. Column chromatography with the same solvent system led to reduced yields for the peptide nitrates.
21. +]: Calculated: 468.1383, found: 468.1391.