Efficient and Selective Synthesis of <scp>d</scp>-<i>arabino</i>-, <scp>d</scp>-<i>lyxo</i>-, and <scp>d</scp>-<i>xylo</i>-Phytosphingosine from <scp>d</scp>-<i>ribo</i>-Phytosphingosine

Abstract

A new high-yield approach to the regio- and stereoselective synthesis of d-arabino-, D-lyxo-, and D-xylo-phytosphingosines from inexpensive D-ribo-phytosphingosine is described. The synthetic methodologies mainly rely on the selective configurational inversion of the stereocenter through a neighboring group participation mechanism.