ABSTRACT
The strategy used for synthesis of 1′,2,3,3′,4,4′-hexa-O-benzylsucrose (5), having only O-6 and O-6′ unprotected, was similar to the one described for the preparation of penta-O-benzylsucrose.1 Accordingly, reaction of sucrose with 2.2 eqv. of trityl chloride provided the di-tritylated derivative 1 in 50% yield. Benzylation of the remaining hydroxyl groups followed by detritylation with iodine in dichloromethane/methanol2 gave 5. The latter compound was also prepared via an alternative route based on the known conversion of the free sucrose into 6,6′-dichloro-6,6′- dideoxysucrose (3),3 followed by benzylation of the remaining six hydroxyl groups with potassium hydroxide as a base.* Subsequent reaction with tetrabutyl-ammonium acetate afforded the corresponding 6,6′-di-O-acetyl derivative 4, which was followed by transesteri¥cation to give 5 (Scheme 44.1).1
