Desymmetrisation of Biphenyl-Based Carbohydrate Receptors; a Non-Bonding Pillar in One Corner of the Cage

L. Challinor, E. Klein, A. P. Davis*

Synlett. 2008, 14, 2137-2141


We report a new addition to the family of biphenyl-based carbohydrate receptors, derived by replacing one out of four iso­phthalamide (diamide) linkages with the corresponding diester. The alteration results in lower binding constants, perhaps reflecting the entropic penalty for lowering receptor symmetry. However, the synthesis allows access to many related host molecules, with potential for restoring and raising affinities and tuning selectivities.