An Improved, Versatile, and Easily Scalable Synthesis of Sphingomyelins: Application to Stable Isotope Labeling

Abstract

With a view to make conveniently labeled mass spectrometry standards available, a set of deuterated sphingomyelins were prepared by a new expedient, flexible, robust, scalable, and high-yielding synthetic scheme starting from 2-azido-3-O-benzoylsphingosine as the key intermediate. Unlike previously published procedures, this work emphasizes the benefit arising from the choice of the azido function as a masking group for the reactive primary amine during the troublesome, though crucial, phosphorylation step.