Synthesis 2006(9): 1480-1484  
DOI: 10.1055/s-2006-926431
PAPER
© Georg Thieme Verlag Stuttgart · New York

Silicasulfuric Acid/NaNO3 as a New Reagent for the Deprotection of S,S-Acetals under Mild Conditions

Abdol R. Hajipour*a,b, Amin Zareia, Leila Khazdooza, Arnold E. Ruohob
a Pharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran
b Department of Pharmacology, University of Wisconsin Medical School, 1300 University Avenue, Madison, WI 53706-1533, USA
e-Mail: haji@cc.iut.ac.ir;
Further Information

Publication History

Received 9 January 2005
Publication Date:
11 April 2006 (eFirst)

Abstract

An efficient, mild and chemoselective method for the deprotection of S,S-acetal compounds to their corresponding car­bonyl compounds using silicasulfuric acid/NaNO3 is reported.

    References

  • 1 Greene TW. Protective Groups in Organic Synthesis   Wiley; New York: 1981. 
  • 2 Kunz H. Waldmann H. In Comprehensive Organic Synthesis   Vol. 6:  Trost BM. Fleming I. Pergamon; New York: 1991.  p.677-681  
  • 3 Corey EJ. Seebach D. J. Org. Chem.  1966,  31:  4097 
  • 4 Mori Y. Kohchi Y. Suzuki M. J. Org. Chem.  1991,  56:  631 
  • 5 Hajipour AR. Khoee S. Ruoho AE. Org. Prep. Proced. Int.  2003,  35:  527 
  • 6 Kamal A. Reddy PSMM. Reddy R. Tetrahedron Lett.  2003,  44:  2857 
  • 7a Hajipour AR. Mirjalili BF. Zarei A. Khazdooz L. Ruoho AE. Tetrahedron Lett.  2004,  45:  6607 
  • 7b Zolfigol MA. Tetrahedron  2001,  57:  9509 
  • 8a Fuji K. Ichikawa K. Fujita E. Tetrahedron Lett.  1978,  19:  3561 
  • 8b Zolfigol MA. Mirjalili F. Bamoniri A. Karimi Zarchi MA. Zarei A. Khazdooz L. Noei J. Bull. Korean Chem. Soc.  2004,  25:  1414