Toward Creation of a Universal NMR Database for Stereochemical Assignment: The Case of 1,3,5-Trisubstituted Acyclic Systems

Abstract

Using the diastereoisomeric triols 1a – d (Fig. 1) and examples summarized in Fig. 2, the central C-atom of acyclic 1,3,5-triols is demonstrated to exhibit a distinctive chemical shift that is dependent on the 1,3- and 3,5-relative configuration, but is independent of the functionalities present outside of this structural motif. These NMR characteristics are then used to predict the relative configuration of several natural products (Fig. 7). In addition, an example is given to show the possibility of assembling an NMR database for a larger array of functional groups from NMR databases of smaller arrays of functional groups.