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-benzo ylsucrose 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.
Barros
M T
MT
Instituto de Biologia Experimental e Tecnológica, Oeiras, Portugal. mtbarros@dq.fct.unl.pt
Maycock
C D
CD
Thomassigny
C
C
D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013395:Sucrose / Q000031:analogs & derivatives* / Q000737:chemistry*
D004952:Esters; D013395:Sucrose