Chiral objects with a dendritic architecture

Abstract

The synthesis and characterization of both enantiomers of 2-(benzyloxy)-1- [3,5-bis[[3,5-bis(benzyloxy)]benzyloxy]benzyloxy]-3-[[3,5-bis(benzyloxy)]benzyloxy] propane (S-7 and R-7) are described. The chirality is based on the linkage of three constitutionally different, but chemically similar, dendritic wedges with a chiral glycerol derived core. Both enantiomers are synthesized from the same starting material: S-(+)-Solketal. Despite their enantiomeric purity, S-7 and R-7 lack any optical activity and may be regarded as the first macromolecular analogues of the well-known organic molecules with “accidental degeneracy” or “cryptochirality.” Chirality 10:46–52, 1998. © 1998 Wiley-Liss,Inc.