37714-06-0

Usage

Uses

Used in Pharmaceutical Applications:
(S)-1-AMINO-BENZYL PHOSPHONIC ACID is used as a key compound in the development of drugs with antiviral, antibacterial, and antitumor properties. Its unique structure allows for potential interactions with biological targets, making it a valuable candidate for pharmaceutical research and drug design.
Used in Chelating Applications:
In biological systems, (S)-1-AMINO-BENZYL PHOSPHONIC ACID serves as a chelating agent for metal ions. Its ability to form stable complexes with metal ions can be utilized in various applications, such as detoxification processes or the stabilization of metalloenzymes.
Used in Industrial Applications:
(S)-1-AMINO-BENZYL PHOSPHONIC ACID is used as a corrosion inhibitor in industrial settings, particularly for preventing metal corrosion in water systems. Its effectiveness in protecting metals from corrosion makes it a valuable addition to the field of industrial chemistry.

Upstream product

• 88081-74-7 C₃₇H₃₀NO₁₀P 
• 1567841-00-2 (-)-di-(1S,2R,5S)-menthyl (R_S,S_C)-1-phenyl-1-(p-tolylsulfinylamino)-methanephosphonate 
• 18108-22-0 1-amino-1-phenylmethylphosphonic acid 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 1354633-60-5 (S)-bis(2-methoxyphenyl) 1-amino-1-phenylmethylphosphonate 
• 1354633-12-7 (S)-bis(2-methoxyphenyl) [(4-methoxyphenyl)aminophenylmethyl]phosphonate 
• 1186001-35-3 (S,S)-O,O-diethyl[1-{(2'-hydroxynaphth-1'-yl)}(phenyl)methylamino]-1-(phenyl)methylphosphonate 
• 1155765-55-1 (S)-diphenyl 1-amino-1-phenylmethylphosphonate 
• 84044-04-2 diphenyl [1-(1-amino)benzyl]phosphonate 
• 88399-40-0 (S)-(+)-α-(diethoxyphosphonyl)benzyl isocyanate 
• 100-52-7 benzaldehyde 
• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 681035-67-6 O,O-dimethyl (S)-{[(1S)-2-hydroxy-1-phenylethyl]amino}(phenyl)methylphosphonothioate 
• 681035-63-2 O,O-dimethyl (S)-{[(1S)-2-hydroxy-1-phenylethyl]amino}(phenyl)methylphosphonate 

Downstream Products

• 71459-79-5 (S)-1-(Benzyloxycarbonylamino)-phenylmethanephosphonic acid 
• 67564-46-9 (S) dimethyl 1-(benzyloxycarbonylamino)phenylmethylphosphonate 
• 67564-48-1 (S)-Ethyl hydrogen 1-(benzyloxycarbonylamino)-phenylmethanephosphonate 

Relevant academic research and scientific papers

Asymmetric synthesis of α-aminophosphonates via diastereoselective addition of phosphite to chiral imine derivatives

One pot three component reactions employing homochiral (1S)-(+)-camphorsulfon-amide-derived carbamate, aldehydes and diethyl phosphite at 0°C was found to give protected (S)-α-aminophosphonates in high enantiomeric purities.

Double asymmetric induction in the synthesis of enantiomeric α-aminophosphonic acids mediated by sulfinimines

A double asymmetric induction in the synthesis of α-aminophosphonic acids is described. It involves the nucleophilic addition of anions of enantiomeric dimenthyl phosphites to both (+)-(S)- and (-)-(R)-enantiomers of N-(p-tolylsulfinyl)benzaldimine and subsequent acidic hydrolysis of the adducts formed. The match and mismatch effects were observed.

Biocatalyzed kinetic resolution of racemic mixtures of chiral α-aminophosphonic acids

Several fungal species namely: Aspergillus niger, Aspergillus parasiticus, Penicillium funiculosum, Trigonopsis variabilis and two different strains of Fusarium oxysporum were tested toward racemic mixtures of following phosphonic acids: 1-amino-2-methylp

Direct enantioselective three-component kabachnik-fields reaction catalyzed by chiral bis(imidazoline)-zinc(II) catalysts

A direct three-component reaction of aldehydes, amines and diaryl phosphites was catalyzed by a zinc(II) complex of 1,3-bis(imidazolin-2-ly) pyridine (pybim) giving the corresponding α-aminophosphonates in good yield with good enantioselectivity. The reac

1-(a-Aminobenzyl)-2-naphthol: A new chiral auxiliary for the synthesis of enantiopure a-aminophosphonic acids

A new diastereoselective synthesis of a-aminophosphonates has been developed, based on the reaction, in the presence of trifluoroacetic acid, of trialkyl phosphites with chiral imines derived from (R)- or (S)-l-(ot- aminobenzyl)-2-naphthol. The reaction p

Organocatalytic enantioselective hydrophosphonylation of sulfonylimines having a heteroarenesulfonyl group as a novel stereocontroller

Organocatalytic enantioselective hydrophosphonylation of imines having the a heteroarenesulfonyl group afforded the respective products with high enantioselectivity. Both enantiomers of α-amino phosphonates were obtained by using different Cinchona alkalo

Straightforward synthesis of depsiphosphonopeptides via Mannich-type multicomponent condensation

A straightforward method for the synthesis of depsiphosphonopeptides via a Mannich-type multicomponent condensation of simple starting materials, such as benzyl carbamate, aldehydes, and 1-carbethoxyalkyl phosphorodichloridites, was developed. Compared to

Stereoselective Addition of Dimethyl Thiophosphite to Imines

Dimethyl thiophosphite (DMTP) was synthesized from dimethyl phosphite, and the diastereoselective addition of DMTP to benzaldimines bearing chiral auxiliary groups was examined. Yields of the product α -aminophosphonothionates ranged from 17% to 75% after chromatography. The addition of DMTP to the benzaldimine derived from (S)-phenylglycinol afforded the highest diastereoselectivity (83:17), whereas addition of DMTP to the benzaldimine derived from threonine methyl ester and alanine methyl ester were far less diastereoselective, affording 38:62 and 61:39 ratios, respectively. Addition of DMTP to the benzaldimine derived from (R)-α-methylbenzylamine (78:22) and (S)-serine methyl ester (73:27) were intermediate in selectivity. DMTP addition to the imines formed between serine methyl ester and acetaldehyde and isobutyraldehyde gave 55:45 and 70:30 ratios, respectively, with the diastereoselectivity corresponding roughly to the size of the α-alkyl group. The stereochemistry of the newly formed α-stereocenters resulting from the addition of DMTP to (S)- and (R)-phenylglycinol benzaldimines was confirmed by conversion of the product α-aminophosphonothionates to the known enantiomers of phosphonophenylglycine.

A new efficient procedure for asymmetric synthesis of α-aminophosphonic acids via addition of lithiated bis(diethylamino)phosphine borane complex to enantiopure sulfinimines

The addition of lithiated bis(diethylamino)phosphine borane complex to enantiopure p-toluenesulfinimines is highly diastereoselective, affording the corresponding addition products with high efficiency (yields from 72 to 100%). The addition products were readily converted into α-amino-α-arylmethylphosphonic acids with high enantiomeric purities (from 72 to >98%).

Asymmetric synthesis of aminophosphonic acids

A new synthesis of chiral α- and β-aminophosphonic acids is described which involves a highly diastereoselective addition of phosphite and phosphonate anions to enantiopure sulfinimines.