Abstract

SA, Marcus M.; SILVEIRA, Gustavo P.; CARO, Miguel S. B.  and  ELLENA, Javier. Synthesis of novel O-acylated-D-ribono-1,5-lactones and structural assignment supported by conventional NOESY-NMR and x-ray analysis. J. Braz. Chem. Soc. [online]. 2008, vol.19, n.1, pp. 18-23. ISSN 0103-5053.  http://dx.doi.org/10.1590/S0103-50532008000100004.

A practical method for the structural assignment of 3,4-O-benzylidene-D-ribono-1,5-lactones and analogues using conventional NMR techniques and NOESY measurements in solution is described. 2-O-Acyl-3,4-O-benzylidene-D-ribono-1,5-lactones were prepared in good yields by acylation of Zinner’s lactone with acyl chlorides under mildly basic conditions. Structural determination of 2-O-(4-nitrobenzoyl)-3,4-O-benzylidene-D-ribono-1,5-lactone was achieved by single crystal x-ray diffraction, which supports the results based on spectroscopic data.

Keywords : O-acyl-D-ribono-1,5-lactones; D-ribono-1,4-lactones; structural elucidation; sugar lactones; acylation.