Diastereo- and enantio-selective binding of octyl glucosides by an artificial receptor

1 H NMR titration experiments have been used to measure the association constants between tetrahydroxycholaphane 1a and the octyl glucosides 2-5; the cholaphane has been shown to discriminate quite effectively between the stereoisomers, showing a diastereoselectivity of ca. 5.5:1 in respect of 2 and 3, and an enantioselectivity of ca. 3:1 in respect of 3 and 5.