The synthesis of phosphonic acids derived from homocysteine via transesterification reactions

Abstract

An efficient methodology for the synthesis of S-substituted derivatives of phosphonohomocysteine has been developed. It starts from the corresponding thiols and is based on a synthetic sequence consisting of (i) the Kabachnik-Fields reaction, (ii) the transesterification of the diphenylphosphoryl moiety and (iii) the acidic deprotection of the phosphoryl and amino groups. The proposed synthetic procedures describing syntheses of phosphonohomocysteine precursors with di-tert-butylphosphoryl and tert-butyloxycarbonylamino groups could be useful for the preparation of novel S-substituted phosphonohomocysteine derivatives.