125402-12-2

Upstream product

• 65600-74-0 ethyl diethoxymethylphosphinate 
• 125402-10-0 ethyl benzhydrylaminomethyl(diethoxymethyl)phosphinate 
• 119-61-9 benzophenone 
• 125402-11-1 aminomethyl-(diethoxymethyl)-phosphinic acid ethyl ester 

Downstream Products

• 125402-33-7 ethyl 1-(benzhydrylideneamino)-3-ethoxycarbonylpropyl(diethoxymethyl)phosphinate 
• 125402-45-1 diethyl <1,5-bis(benzhydrylideneamino)pentane-1,5-diyl>bis(diethoxymethylphosphinate) 
• 125402-35-9 {1-(Benzhydrylidene-amino)-2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethyl}-diethoxymethyl-phosphinic acid ethyl ester 
• 125402-16-6 [1-(Benzhydrylidene-amino)-nonadecyl]-diethoxymethyl-phosphinic acid ethyl ester 
• 125402-23-5 [1-(Benzhydrylidene-amino)-2-(4-benzyloxy-phenyl)-ethyl]-diethoxymethyl-phosphinic acid ethyl ester 
• 125402-32-6 3-(Benzhydrylidene-amino)-3-(diethoxymethyl-ethoxy-phosphinoyl)-propionic acid ethyl ester 
• 125402-21-3 [1-(Benzhydrylidene-amino)-2-(4-bromo-phenyl)-ethyl]-diethoxymethyl-phosphinic acid ethyl ester 
• 125402-20-2 [1-(Benzhydrylidene-amino)-2-(4-chloro-phenyl)-ethyl]-diethoxymethyl-phosphinic acid ethyl ester 
• 125402-19-9 [1-(Benzhydrylidene-amino)-2-(4-fluoro-phenyl)-ethyl]-diethoxymethyl-phosphinic acid ethyl ester 
• 125402-29-1 [1-(Benzhydrylidene-amino)-6-bromo-hexyl]-diethoxymethyl-phosphinic acid ethyl ester 
• 125402-26-8 [1-(Benzhydrylidene-amino)-2-cyclohexyl-ethyl]-diethoxymethyl-phosphinic acid ethyl ester 
• 125402-22-4 [1-(Benzhydrylidene-amino)-2-p-tolyl-ethyl]-diethoxymethyl-phosphinic acid ethyl ester 
• 125402-17-7 [1-(Benzhydrylidene-amino)-3-phenyl-propyl]-diethoxymethyl-phosphinic acid ethyl ester 
• 125402-30-4 [1-(Benzhydrylidene-amino)-5-bromo-pentyl]-diethoxymethyl-phosphinic acid ethyl ester 

Relevant academic research and scientific papers

Oxidative deprotection of diphenylmethylamines

(formula presented) The diphenylmethyl amino protecting group can be efficiently removed by initial oxidation of the amine to an imine by 2,3-dichloro-5,6-dicyanobenzoquinone. The resulting imine can then be easily hydrolyzed under mildly acidic conditions. This method is particularly well suited for the preparation of α-amino phosphinates and α-amino phosphonates.

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).