SYNTHESIS AND REACTIONS OF tert-BUTYLDIPHENYLSILYL ETHERS OF SUCROSE

Article abstract of DOI:10.1016/S0008-6215(00)80792-2

The reaction of sucrose with 1.1 mol. equiv. of tert-butyldiphenylsilyl (t-BDPS) chloride in pyridine in the presence of 4-dimethylaminopyridine gave the crystalline 6'-t-BDPS ether 1 in 49percent yield, without recourse to column chromatography.Compound 1 was transformed into the 4,6,1'-trichloride by using sulphuryl chloride.When the silylation reaction of sucrose was performed with 3 mol. equiv. of the reagent, chromatography gave the crystalline 6,6'-di-t-BDPS ether and the 6,1',6'-tri-t-BDPS ether 9 in yield of 78 and 18.7percent, respectively.Compound 9 was obtained as the major product on treatment of sucrose with 4.6 mol.equiv. of the silylating reagent.Removal of the silyl protecting-group in 6,6'-di-O-ter-butyldiphenylsilylsucrose hexabenzoate, using tetrabutylammonium fluoride, proceeded smoothly, but with 4->6 migration of the benzoate.