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 perbenzoylated and deprotected at OH-1′ with tetrabutylammonium fluoride (86%). An analogous sequence with the corresponding O-acetylated sucrose derivative and tetrabutylammonium fluoride as desilylating agent resulted in a lower yield of the C-1′ hydroxy derivative.