6,6'-Di-O-t-butyldimethylsilylsucrose: Studies on the rearrangements accompanying deblocking of such silyl ethers

Abstract

Use of limited amounts of t-butyldimethylsilyl chloride with sucrose in pyridide have led to the 6,6'-disilyl ether isolable in 36% yield without chromatography. Removal of the silyl ether groups from 2,3,4,1',3',4'-hexa-O-acyl- 6,6'-di-O-t-butyldimethylsilyl-sucroses has been studied with dilute acid and with tetrabutylammonium fluoride. The former reagent gave the expected hexa-O-acylsucroses, whereas the latter method yielded 2,3,6,1',3',4'-hexa-O-acylsucroses formed by a 4 → 6 acyl migration in the D-glucose moiety.