Application of the Dibenzoate Chirality Method To Determine the Absolute Configuration of Glycerols and Related Acyclic Alcohols

Article abstract of DOI:10.1021/jo00288a024

Circular dichroism (CD) and nuclear magnetic resonance spectroscopy (NMR) were applied to the study of various chiral 1,2-(or 2,3)-di-O-benzoyl-sn-glycerols (substituent at sn-C1 or -C3 = cetyloxy, OBn, OMe, hexadecanoyloxy, OAc, penta-O-acetyl-β-D-glucopyranosyl, H, N3, Br, OTs, and OSi(Me)2-t-Bu).All compounds gave positive or negative exciton couplet (CD) peaks, reflecting the absolute configuration at C2 and conformational preference about the vicinal di-O-benzoates.The results were confirmed by conformational analyses using 1H NMR spectroscopy and led to theproposal of a new method to determine the absolute configuration of asymmetric glycerols.