Abstract

CRUZ-GREGORIO, Silvano et al. Highly Efficient Inversion of the C-3 Configuration in 1,2-0-Isopropylidenefuranose Derivatives by an Adapted Swern Oxidation/Sodium Borohydride Reduction Protocol in One Pot. J. Mex. Chem. Soc [online]. 2005, vol.49, n.1, pp.20-23. ISSN 1870-249X.

One pot Swern oxidation-sodium borohydride reduction of 1,2-O-isopropylidenefuranose derivatives having the D-gluco or D-xylo configurations led to the corresponding stereoisomers resulting from the stereoselective inversion of C-3. This method is a simple adaptation to the traditional procedure that consists in quenching the Swern oxidation at -60 °C with a mixture of H₂O/EtOH (1:4), in which NaBH₄ is dissolved. Thus, the inversion of the configuration at C-3 of 1,2-O-isopropylidenefuranose derivatives is accomplished in yields up to 98%.

Keywords : Inversion of the configuration; Swern oxidation-sodium borohydride reduction in one pot.