Efficient synthesis of the four diastereomers of phosphothreonine from lactaldehyde

Article abstract of DOI:10.1016/0957-4166(96)00164-4

The four stereoisomers of phosphothreonine are obtained in high diastereomeric purity based on the stereoselective addition of trimethylsilyldiethylphosphite (TMSDEP) to scalemic N-trimethylsilyl-lacticimine and addition of TMSDEP to lactaldehyde followed by Mitsunobu inversion of the corresponding α-hydroxy-β-silyloxy phosphonate.