Synthesis of amphiphilic lactose-substituted polyether dendrimers

Previously, we reported synthesis of amphiphilic polyether dendrimers having a sugar residue at the core, designed to create a new biomedical material with controlled sugar alleys having intervals on a nanoscale by organization, and the plane arrangement of the dendrimers was shown to be able to control at nano-level. In this report, we synthesized amphiphilic n-decyl-terminal polyether dendrimers having a lactose or galactose residue at the core. The core-lactose- or galactose-substituted poly(ethylene glycol) dendrimer was afforded by Schmidt glycosylation between the core-hydroxy-type n-decyl-terminal aliphatic polyether dendrimer and 4-0-(2,3,4,6-tetra-O-acetyl-β-D- galactopyranosyl)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate or 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl trichloroacetimidate followed by deacetylation. Chemical structures of the dendrimers were determined by¹H-NMR, ¹H-¹H COSY and MALDI-TOF MS analyses.