Synthesis 2004(7): 1033-1036  
DOI: 10.1055/s-2004-822329
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Regioisomeric Azidobutanediols

Marion Aepkers, Bernhard Wünsch*
Institut für Pharmazeutische und Medizinische Chemie der Westfälischen Wilhelms-Universität Münster, Hittorfstraße 58-62, 48149 Münster, Germany
Fax: +49(251)8332144; e-Mail: wuensch@uni-muenster.de;
Further Information

Publication History

Received 19 January 2004
Publication Date:
02 April 2004 (online)

Abstract

Investigations to control the regioselectivity during the acetalization of pivalaldehyde (7) with butane-1,2,4-triol (4) were performed. Thermodynamic control led to the regioisomeric acetals 8 and 9 in the ratio 76:24, whereas kinetic control favored the five-membered acetal 9 (8/9 30:70). Tosylation, nucleophilic substitution with NaN3, and subsequent methanolysis of the regioisomeric acetals 8 and 9 provided the regioisomeric 4-azidobutanediols 5 and 6, which are considered as valuable building blocks for the synthesis of novel NMDA-receptor antagonists.

    References

  • 1 Hardie WR. Hidalgo J. Halverstadt IF. Allen RE. J. Med. Chem.  1966,  9:  127 
  • 2 Thurkauf A. Zenk PC. Balster RL. May EL. George C. Carroll FI. Mascarelle SW. Rice KC. Jacobson AE. Mattson MV. J. Med. Chem.  1988,  31:  2257 
  • 3 Thurkauf A. Mattson MV. Richardson S. Mirsadeghi S. Ornstein PL. Harrison EA. Rice KC. Jacobson AE. Monn JA. J. Med. Chem.  1992,  35:  1323 
  • 4 Aepkers M. Wünsch B. Arch. Pharm. Pharm. Med. Chem.  2004,  337: 
  • 5 Lehmann J. Ziser J. Carbohydr. Res.  1987,  169:  53 
  • 6 Brückner R. Reaktionsmechanismen: Organische Reaktionen, Stereochemie, moderne Synthesemethoden   Spektrum-Verlag; Heidelberg: 1996.  p.257 
  • 7 Wünsch B. Diekmann H. Liebigs Ann.  1996,  69 ; and references cited therein
  • 8 Still W. Kahn M. Mitra A. J. Org. Chem.  1978,  43:  2923