Preparation of sucrose heptaesters unsubstituted at the C-1 hydroxy group of the fructose moiety via selective O-desilylation

Selective O-desilylation of 6,1',6-tri-O-tert-butyldiphenylsilyl-2,3,4,3',4 '-penta-O-benzoylsucrose with hydrofluoric acid in acetonitrile led to the 1'-O-tert-butyldiphenylsilyl derivative (96% yield), which was further perb enzoylated and deprotected at OH-1' with tetrabutylammonium fluoride (86%). An analogous sequence with the corresponding O-acetylated sucrose derivati ve and tetrabutylammonium fluoride as desilylating agent resulted in a lowe r yield of the C-1' hydroxy derivative. (C) 2000 Elsevier Science Ltd. All rights reserved.