Síntese de glicoglicerolipídios contendo pirimidinas a partir do glicerol e tri-O-acetil-D-glucal

Abstract

In this work, new glycoglycerolipids conjugates with triazole and pyrimidines were synthesized. Firstly, tri-O-acetyl-D-glucal 23 reacted with glycerol sulfite 58 in the presence of BF3Et2O to leads to diasteroisomers mixture of 2,3-unsaturated O-glucoside in 78% yield. Afterwards, reaction with sodium azide afforded the azido-glycero-glucoside 8-R,S-60 in 85% yield. Next, azido-glycoglycerolipid 61c was obtained in 56% yield after reaction with lauroyl chloride in the presence of DMAP/Et3N. The reaction of propargyl bromide with uracile, thymine or fluor-uracile, using K2CO3/DMF at room temperature leads to mono- and bis-alkylated pyrimidines 62-63 with yields of 20-35% and 74-86%, respectively. Thus, the propargylated pyrimidines were coupled with azido-glycoglycerolipid 61c via CuI-catalysis to furnish glycoglycerolipids 64a-c and 65a-c in yields ranging from 67 to 75% and from 43 to 48%, respectively.