A method for the synthesis of unsymmetric bisphosphoric analogs of α-amino acids.

ABSTRACT: Herein, we describe the first universal strategy for the synthesis of unsymmetric phosphonyl-phosphinyl and phosphonyl-phosphinoyl analogs of N-protected 1-aminobisphosphonates. The proposed user-friendly procedure, based on a one-pot reaction of the α-ethoxy derivatives of phosphorus analogs of protein and non-protein α-amino acids with triphenylphosphonium tetrafluoroborate and an appropriate phosphorus nucleophile (diethyl phenylphosphonite or methyl diphenylphosphinite), provides good to very good yields of 53-91% under mild catalyst-free conditions (temperature: rt to 40 °C, time: 1 to 6 hours). The progress of the transformation, running through the corresponding phosphonium salt as a reactive intermediate, was monitored by ³¹P NMR spectroscopy, which is a convenien

SUBMITTER: Kuznik A 

PROVIDER: S-EPMC10288832 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature