Arkadiusz Listkowski, Sławomir Jarosz
Recently we elaborated a convenient route to 1’,2,3,3’,4,4’-hexa-O-benzylsucrose (1) from free sucrose.1 This compound was applied for the preparation of macrocycles containing the sucrose unit. Reaction of 1 with several ditosylates under standard conditions (used for construction of such macrocycles) afforded chiral crown ether analogues 2.
The benzyl protecting groups can be conveniently removed by simple hydrogenolysis. The complexation of the cations of the first group by these derivatives was studied by MS and NMR methods. The newly formed macrocycles as well as their deprotected derivatives were used for enantioselective comlexation of chiral amines.
1. Jarosz, S.; Listkowski, A. J. Carbohydr. Chem., 2003, 22, 753.
2. review on modification of sucrose at the terminal positions: Jarosz, S.; Mach, M., Eur. J. Org. Chem., 2002, 769.