Study On Synthesis Of Glucose Tetraesters And Glucoside Tetraesters

Glucose tetraesters as an important potential of fragrant substances in tobacco, hasimportant application value. In this paper, D-glucose was used as raw material, first ofall the reactive anomeric centre was selectively protected to generate glucopyranoside.We also studied the synthesis of methyl, benzyl and allyl glucoside and the deprotectingof the reactive anomeric centre, finally allyl group was chosen as the protecting groupof the reactive anomeric centre, then through a series of the selectiveprotecting-deprotecting and acylation of the hydroxyl group, we synthesised allyl2,3,4,6-tetra-O-acetyl-D-glucopyranoside, allyl6-O-acetyl-2,3,4-tri-O-isovaleryl gluco-pyranoside and allyl6-O-acetyl-2,3,4-tri-O-(3-methyl valeryl) glucopyranoside, furtherusing effective catalytic system of N-bromosuccinimide/boron trifluoride etherate tocatalyze the removing of allyl group, giving2,3,4,6-tetra-O-acetyl-D-gluco-pyranose,6-O-acetyl-2,3,4-tri-O-isovaleryl glucopyranose and6-O-acetyl-2,3,4-tri-O-(3-methylvaleryl) glucopyranose. The chemical structure of products were characterized bynuclear magnetic resonance (NMR) and high-resolution mass spectrometer (HRMS).In addition, in reference to the preparation of glucose esters on the basis of thestudy of our laboratory, we studied the optimum reaction conditions of the deprotectingof the reactive anomeric centre of allyl2,3,4,6-tetra-O-acetyl-D-glucopyranoside, theacylation of2-,3-and4-hydroxyl group of allyl6-O-tert-butyldiphenylsilyl-D-gluco-pyranoside and the acetylation of6-hydroxyl group of allyl2,3,4-tri-O-acyl-D-gluco-pyranoside. The reaction route was further optimized, the difficulty of after treatmentwas redused to a certain extent, the reaction yield was increased. Providing a goodreference to achieve the synthesis of sucrose tetra-esters or disaccharide tetra-esters.