121722-22-3

Upstream product

• 125402-32-6 3-(Benzhydrylidene-amino)-3-(diethoxymethyl-ethoxy-phosphinoyl)-propionic acid ethyl ester 
• 125742-18-9 ethyl 4-oxo-azetidin-2-yl(diethoxymethyl)phosphinate 
• 62415-63-8 formylacetic acid oxime 
• 53676-35-0 diethyl 2-(acetylaminomethylidene)malonate 

Downstream Products

• 204063-97-8 3-(N-(benzyloxycarbonyl)amino)-3-hydroxyphosphinyl propanoic acid 

Relevant academic research and scientific papers

Synthesis of phosphinic and phosphonic analogs of aspartic acid

Approaches to the synthesis of 1-amino- and 2-amino-2-carboxyethylphosphinic and -phosphonic acids have been studied. A convenient method for the preparation of phosphinic acids is the reactions of ethyl diethoxymethylphosphonite with ethyl acetamidomethylenemalonate and ethyl 2-acetamidoacrylate.

DIETHOXYMETHYLPHOSPHONITES AND PHOSPHINATES. INTERMEDIATES FOR THE SYNTHESIS OF α,β- AND γ-AMINOALKYLPHOSPHONOUS ACIDS

New building blocks for the synthesis of functional alkyl phosphonous acids are described.Diethoxymethylphosphonites and phosphinates are readily prepared and undergo reactions typical of phosphites and phosphonates.The products are stable to chemical transformations, readily handled and purified, and easily transformed to the phosphonous acids.

Synthesis of 1-Aminoalkylphosphinic Acids. Part 2. An Alkylation Approach

Aminomethylphosphinic acid (7), protected at nitrogen as the imine derived from benzophenone and at phosphorus as the diethylacetal and ethyl ester , undergoes facile LDA-induced alkylation.Treatment with primary alkyl halides affords, on product hydrolysis, a versatile route to phosphinic analogues of α-amino carboxylic acids.Analogues of alanine, valine, leucine, phenylalanine, tyrosine, histidine, and aspartic and glutamic acids are thus prepared; the phosphonic histidine analogue (23b) can be prepared similarly from the imine phosphonate diester (21).Intra- and inter-molecular dialkylation reactions provide analogues of 1-aminocyclopropanecarboxylic acid (14) and 2,6-diaminoheptanedioic acid (16).Benzyl bromide alkylation of (25a) and (30a), where the nitrogen is protected as the imine of the 2-hydroxypinan-3-one chiral auxiliary (24) or (29), is diastereospecific leading to asymmetric synthesis of either (+)- or (-)-phenylalanine analogues; this selectivity is compared to that shown by the corresponding chiral imine phosphonate (25b) and imine carboxylate (25c).