An eco-friendly and improved method for the Ferrier sulfonamidoglycosylation of tri-O-acetyl-D-glucal with different N-nucleophiles has been developed using Er(OTf)3 in 2-MeTHF. The conversion of 3,4,6-tri-O-acetyl-D-glucal into 2,3-unsaturated-N-pseudoglycals with sulphonamides previously prepared using the same method as environmentally friendly and the subsequent addition of glucale can be realized in a few minutes with good yields and preferential a-anomeric selectivity. Sulfonamides continue to play an important role in chemotherapy, despite the abandonment of their use as antibiotics. Is known that several sulfonamides show anticancer properties [1] and are antiproliferative activity against human hepatocellular carcinoma in the micromolar range. These have also been reported to have potent biological activities in terms of new cancer drugs, with phenotypic screens and gene expression analysis in particular for the E7010, E7070, ER-67865 and ER-68487 (Figure 1).[3] Taking into account the Anastas and Warner's 12 Principles of Green Chemistry, we looked at the 2-MeTHF as a very compelling case against toxics solvents. In continuation of our interest in exploring the utility of Er(OTf)3 as a Lewis acid catalyst in the glycal chemistry, we developed a practical low-cost environmentally friendly procedure for their N-glycosylation in 2-MeTHF. We now wish to report a mild and efficient general method for the synthesis of sulphonamides before and their subsequent use for the reactions of Ferrier azaglycosylation

ECO-FRIENDLY PROTOCOL FOR FERRIER AZAGLYCOSYLATION PROMOTED BY ER(OTF)3 IN 2-METHF

NARDI M;
2015

Abstract

An eco-friendly and improved method for the Ferrier sulfonamidoglycosylation of tri-O-acetyl-D-glucal with different N-nucleophiles has been developed using Er(OTf)3 in 2-MeTHF. The conversion of 3,4,6-tri-O-acetyl-D-glucal into 2,3-unsaturated-N-pseudoglycals with sulphonamides previously prepared using the same method as environmentally friendly and the subsequent addition of glucale can be realized in a few minutes with good yields and preferential a-anomeric selectivity. Sulfonamides continue to play an important role in chemotherapy, despite the abandonment of their use as antibiotics. Is known that several sulfonamides show anticancer properties [1] and are antiproliferative activity against human hepatocellular carcinoma in the micromolar range. These have also been reported to have potent biological activities in terms of new cancer drugs, with phenotypic screens and gene expression analysis in particular for the E7010, E7070, ER-67865 and ER-68487 (Figure 1).[3] Taking into account the Anastas and Warner's 12 Principles of Green Chemistry, we looked at the 2-MeTHF as a very compelling case against toxics solvents. In continuation of our interest in exploring the utility of Er(OTf)3 as a Lewis acid catalyst in the glycal chemistry, we developed a practical low-cost environmentally friendly procedure for their N-glycosylation in 2-MeTHF. We now wish to report a mild and efficient general method for the synthesis of sulphonamides before and their subsequent use for the reactions of Ferrier azaglycosylation
2-MeTHF; Ferrier; green chemistry
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/20.500.12078/1662
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