Efficient synthesis of sphingosine-1-phosphonate and homo-sphingosine-1-phosphonate

Article abstract of DOI:10.1016/S0960-894X(97)00047-4

Sphingosine can be selectively transformed into 2-N,3-O-protected 1-O-mesyl derivative 8. Transformation into the bromide, Michaelis-Arbusov reaction with trimethyl phosphite, and then removal of all protective groups with LiOH afforded sphingosine-1-phosphonate (4) in high overall yield. Chain extension of 8 with KCN and ensuing reduction led to homosphingosine derivative 10 and also to homo-1-deoxysphingosine (5). 1-O-Mesylation of 10 led via the same sequence of reactions finally to homo-sphingosine-1-phosphonate (6).