Regioselective acylation of 2,1':4,6-di-O-isopropylidene-D-sucrose (2)
with trans-cinnamoyl chloride gave intermediate 3, which was transfor
med in four steps into niruriside (1) in 23% overall yield. On the oth
er hand, conversion of 2 into 1',2,4,6-tetra-O-acetylsucrose 10 follow
ed by cinnamoylation gave (1) in 41% overall yield.