Desenvolvimento de uma nova metodologia sintética para a hidrólise quimiosseletiva de o - gligosídeos 2, 3 - insaturados.

Abstract

Carbohydrates are the most abundant macromolecules polyfunctional nature. These organic compounds may be named as: carbohydrates, sugars, saccharides or carbohydrates, most commonly, a name that is derived from its general empirical formula Cn(H2O)n. Carbohydrates, but specifically glycosides, present numerous medical and technological applications. In view of the above, and aware of the importance of glycosides, this paper aims to propose a new synthetic methodology for the chemioselective hydrolysis of O-glycosides 2,3-unsaturated to obtain the 4,6-diol 2,3-dideoxy-α-D-erythro-hex-2-enopiranosídeos. Accordingly, it was initially synthesized tri-O-acetyl-D-glucal with 95% yield from successive structural modifications of D-glucose. Then, the tri-O-acetyl-D-glucal was subjected to the rearrangement to take Ferrier O-glycosides 2,3-unsaturated yields ranging 77 to 97% using montmorillonite K-10 as Lewis acid. Finally, the 2,3-O-glycosides unsaturated underwent reaction to take chemoselective hydrolysis to the corresponding diols, which were obtained with yields ranging 92 to 98% in reaction times of five minutes. Additionally, all synthesized compounds were characterized by various spectroscopic techniques (IR, 1H and 13C NMR and specific rotation).