Síntese do Tri-O-Acetil-D-Glucal utilizando irradiação de ultrassom e bioensaio frente à Artemia Salina Leach de Oglicosídeos 2, 3 - insaturados.

Abstract

Sugars in combination with other macromolecules perform important functions for the maintenance of life. Because its diverse biological functions, technology and industry, the number of research groups exploring the chemistry of sugars is growing and O-glycosides are a class that has been gaining attention because they are important structures used as precursors in the synthesis of biologically active molecules. In parallel, the use of the ultrasound irradiation is an alternative to improve the reaction by reducing the reaction time and in some cases with increased yield. In addition, the literature describes the use of the larvae of Artemia salina Leach as a good preliminary test to evaluate the toxicity of compounds due to their simplicity, reproducibility, low cost and to present the results of the correlations compared to other toxicological activity, biological and pharmacological. Considering these arguments, this paper proposes to introduce a new method for the synthesis of 3,4,6-tri-O-acetyl-D-glucal by ultrasonic irradiation. After promote the reaction between 3,4,6-tri-O-acetyl-D-glucal with different alcohols catalyzed by montmorillonite K-10 to obtain the 2,3-unsaturated O-glycosides by Ferrier rearrangement. Finally carry out the assessment toxicological on Artemia salina Leach of the compounds obtained. As a result of the 3,4,6-tri-O-acetyl-D-glucal was obtained in 95% yield in a reaction time four times lower when compared to the methodology described in the literature. 2,3-Unsaturated O-glycosides were obtained in yields ranging from 79-96%. And bioassays showed that five compounds showed low toxicity (LC50> 1000 ppm) and three moderate toxicities compounds (LC50 <1000 ppm) against the larvae of Artemia salina Leach.