INTERACTION BETWEEN ACETONE AND SOME CARBOHYDRATE BENZENEBORONATES: SELECTIVE ACETONOLYSIS OF 2-PHENYL-1,3,2-DIOXABOROLANES

Article abstract of DOI:10.1016/S0008-6215(00)85673-6

Treatment of D-glucitol 1,3:2,4:5,6-tris(benzeneboronate), D-mannitol 1,2:3,4:5,6-tris(benzeneboronate), and α-D-glucofuranose 1,2:3,5-bis(benzeneboronate) with acidified acetone, followed by chromatography using lyotropic solvents, gives 5,6-O-isopropylidene-D-glucitol, 1,2-O-isopropylidene-D-mannitol, and 1,2-O-isopropylidene-α-D-glucofuranose, respectively, in yields of 43-78percent.