Abstract
A comvenient method for the preparation of N-acyl O-TMS derivatives of sphingolipid bases is described; i.e., O-TMS derivatives of the bases, which are obtained by the HMDS+TMCS / pyridine treatment, are reacted with acid anhydride to give the desired N-acyl-O-TMS compounds.
The reaction of these bases with BSA/acetonitrile gave N, O-TMS derivatives which did not react with acid anhydrides, since the amino group was protected by the TMS group.
The above method was applied to several bases and the structures of the resulting products were determined by GLC and GLC-MS. N-Acyl O-TMS derivatives of synthetic Cn-dihydroshingosines were prepared by the present method. The erythro/threo ratios of their derivatives were the same as those determined using BSA. The present method can be easily carried out in a very short period of time. MS analyses for both O-TMS and N-acyl O-TMS derivatives are possible without having to prepare the N-acyl derivatives of sphingosine bases.
