2-hydroxymethyl-2-propylpropane-1,3-diol in the synthesis of acetal-like and phosphacyclic lipids

New acetal-like and phosphacyclic lipids were synthesized on the basis of 2-hydroxymethyl-2-propylpropane-1,3-diol. The initial triol was initially treated with higher aldehydes to obtain the corresponding acetals, which were phosphorylated with chlorobis(diethylamino)phosphine. Intermediate phosphorodiamidites were oxidized (without isolation) with phenyliodane oxide or subjected to sulfurization or selenization. Bicyclic phosphite derived from 2-hydroxymethyl-2-propylpropane-1,3-diol was acylated with hexadecanoyl chloride to give 2-chloro-4-propyl-1,3,2-dioxaphosphinan-4-ylmethyl hexadecanoate, and methanolysis of the latter, followed by sulfurization, afforded 2-methoxy-5-propyl-2-thioxo-1,3,2λ⁵-dioxaphosphinan-5-ylmethyl hexadecanoate as a new phosphacyclic lipid.