Stereospecific reduction of 2,3-epoxybutanoic acid. Synthesis of (R,R)- and (S,S)-3-hydroxybutanoic-2-d acid and S-tert-butyl 3-acetoxythiobutanoate-2-d Academic Article uri icon

abstract

  • Reduction of 2,3-epoxybutanoic acid (2) with sodium borodeuteride provides a stereospecific synthesis of 3-hydroxybutanoic-2-d acid (3). This route should be of general utility in stereospecific syntheses of metabolically important 3-hydroxyalkanoic acid derivatives labeled at C-2. Metal ions seem to play an important role in the relative rates of nucleophilic attack at the α- and β-carbon atoms of 2. Compound 3 was converted to S-tert-butyl 3-acetoxythiobutanoate-2-d (1) with virtually no H-D exchange; the mixed anhydride method proved more effective than the DCC method for the thioester synthesis. © 1981, American Chemical Society. All rights reserved.

author list (cited authors)

  • Mohrig, J. R., Vreede, P. J., Schultz, S. C., & Fierke, C. A.

citation count

  • 13

publication date

  • November 1981