Uses
2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone is used as a reactant to synthesize various glucoside containing compounds as selective SGLT2 inhibitors for the treatment of type 2 diabetes mellitus.
Synthesis
Example XXI Synthesis of 2,3,4,6-tetra-O-benzyl-D-glucopyranoside: 4 g of freshly activated 4 molecular sieves and 3.3 g of N-methylmorpholine-N-oxide were added to a 140 mL solution of dichloromethane containing 10.0 g of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose. After stirring the reaction mixture for 20 minutes at room temperature, 0.3 g of tetrapropylammonium perruthenate was added. Stirring was continued at room temperature for 2 h. Upon completion of the reaction, the reaction solution was diluted with dichloromethane and filtered through a diatomaceous earth pad. The filtrate was washed sequentially with aqueous sodium thiosulfate and deionized water and dried over anhydrous sodium sulfate. After concentration under reduced pressure to remove the solvent, the residue was purified by silica gel column chromatography (eluent: cyclohexane/ethyl acetate, 4:1, v/v). The product was obtained as 8.2 g in 82% yield. Mass spectrum (ESI+): m/z = 539 [M + H]+.
References
[1] Patent: WO2005/92877, 2005, A1. Location in patent: Page/Page column 63
[2] Patent: US2006/189548, 2006, A1. Location in patent: Page/Page column 26-27
[3] Patent: US2006/234953, 2006, A1. Location in patent: Page/Page column 14
[4] Patent: US2007/4648, 2007, A1. Location in patent: Page/Page column 14
[5] Patent: US2007/27092, 2007, A1. Location in patent: Page/Page column 26
