Monosaccharidic Push-pull Butadienes: Versatile Synthetic Intermediates

Abstract

Monosaccharidic push-pull butadienes are interesting building blocks for the synthesis of various heterocyclic and natural products due to their biological prevalence and significant p-electron interactions between donor and acceptor groups. A series of 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy- 2-formyl-D-arabino-hex-1-enitol (2) and 1,5-anhydro-3,4-di-O-benzyl-2-deoxy-2-formyl-L-erythrohex- 1-enitol (4) derived push-pull branched chain sugars have been synthesized by condensation with active methylene compounds using basic aluminum oxide (Al2O3) or anhydrous sodium acetate (NaOAc) at room temperature. The compounds have been fully characterized by spectroscopic techniques and elemental analyses.