Synthesis and chiroptical properties of (naphthyl)ethylidene ketals of carbohydrates in solution and solid state

1,3-Dioxolane- and dioxane-type (1- and 2-naphthyl)ethylidene ketals of p-methoxyphenyl alpha-L-rhamnopyranoside and beta-D-glucopyranoside were prepared and their stereochemistry studied by solution and solid-state circular dichroism, X-ray diffraction, and coupled-oscillator CD calculations on the solid-state and MMFF-calculated geometries. Intermolecular exciton-coupled interactions between the nearby aromatic chromophores in the solid state and different conformers in solution and solid state could be identified as the main reason for the difference between solution and solid-state CDs. (C) 2007 Elsevier Ltd. All rights reserved.