37714-05-9

Usage

Uses

Used in Organic Chemistry:
(R)-1-PHOSPHONO-BENZYLAMINE is used as a ligand for [application reason] enhancing the efficiency and selectivity of metal-catalyzed reactions. Its presence can modulate the reactivity and stereochemistry of the catalyst, leading to improved outcomes in various organic synthesis processes.
Used in Pharmaceutical Synthesis:
(R)-1-PHOSPHONO-BENZYLAMINE is used as a building block for [application reason] the creation of various pharmaceuticals and biologically active compounds. Its unique structure allows for the development of novel drugs with potential therapeutic benefits.
Used in Enzyme Inhibition:
(R)-1-PHOSPHONO-BENZYLAMINE is used as an enzyme inhibitor for [application reason] targeting specific metabolic pathways. By inhibiting certain enzymes, it can potentially influence cellular processes and be utilized in the development of treatments for various diseases.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (R)-1-PHOSPHONO-BENZYLAMINE is used as a research compound for [application reason] exploring its potential biological activities and its role in the development of new therapeutic agents. Its study can lead to a better understanding of its interactions with biological systems and the discovery of new applications in medicine.

Upstream product

• 84044-04-2 diphenyl [1-(1-amino)benzyl]phosphonate 
• 1010692-83-7 dimethyl [(S_S,R)-(+)-(tert-butylsulfinylamino)(phenyl)methyl]phosphonate 
• 156078-35-2 N-<(R)-2-methoxy-1-phenylethyl>amino benzylphosphonic acid 
• 114987-92-7 (+)-(R)-<(hydroxyamino)(phenyl)methyl>phosphonic acid 
• 114987-93-8 (-)-(S)-<(hydroxyamino)(phenyl)methyl>phosphonic acid 
• 1795-31-9 tris(trimethylsilyl) phosphite 
• 66217-71-8 N - ((R)-α-methylbenzyl)amino(phenyl)methylphosphonic acid 
• 18108-22-0 1-amino-1-phenylmethylphosphonic acid 
• 104513-37-3 1-(N-Phenylacetylamino)-1-phenylmethylphosphonic acid 
• 104513-37-3 D-1-(N-Phenylacetylamino)-1-phenylmethylphosphonic acid 
• 862776-58-7 (S)-N-benzylidene-2-methylpropane-2-sulfinamide 
• 1567840-97-4 (+)-di-(1R,2S,5R)-menthyl (S_S,R_C)-1-phenyl-1-(p-tolylsulfinylamino)-methanephosphonate 
• 100-52-7 benzaldehyde 
• 1201762-38-0 C₁₈H₂₂NO₄P 

Downstream Products

• 615264-92-1 (R)-1-benzyloxycarbonylamino-1-phenylmethylphosphonic acid 

Relevant academic research and scientific papers

A Highly Convenient Route to Optically Pure α-Aminophosphonic Acids

Pure diastereomers, obtained simply and directly by reaction of hypophosphorous acid salts of (R)(+) or (S)(-) - N-α-methylbenzylamine with aldehydes, can be simultaneously deprotected and oxidised in one step to provide a highly convenient synthesis of α-aminophosphonic acids in high optical purity.

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.

Highly diastereoselective addition of chiral H-phosphonate to tert-butylsulfinyl aldimines: a convenient approach to (R)-α-aminophosphonic acids

Abstract A highly diastereoselective nucleophilic addition of chiral H-phosphonate, derived from a readily available TADDOL auxiliary, to (S)-N-tert-butylsulfinyl aldimines is reported. The reaction proceeds at room temperature in the presence of potassium carbonate and yields the corresponding aliphatic, aromatic and heteroaromatic α-aminophosphonates with dr >95:5. Subsequent simultaneous removal of both chiral auxiliaries leads to the desired α-aminophosphonic acids in very good yields with an (R)-configuration at the stereogenic α carbon.

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

Highly enantioselective conjugate additions of phosphites to α β-unsaturated N-acylpyrroles and imines: A practical approach to enantiomerically enriched amino phosphonates3

The first highly enantioselective phosphonylation of αβ- unsaturated N-acylpyrroles has been developed. Excellent yields (91-99%) and enantioselectivities (up to >99% enantiomeric excess (ee)) were observed for a broad spectrum of both phosphites and N-ac

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

Catalytic enantioselective pudovik reaction of aldehydes and aldimines with tethered bis(8-quinolinato) (TBOx) aluminum complex

New chiral tethered bis(8-quinolinolato) (TBOx) aluminum(III) complexes effectively catalyze the addition of phosphites to aldehydes and aldimines to give enantioenriched α-hydroxy and α-amino phosphonates in high yields and enantioselectivities with unpr

A new and convenient asymmetric synthesis of α-amino- and α-alkyl-α-aminophosphonic acids using N-tert-butylsulfinyl imines as chiral auxiliaries

Nucleophilic addition of dialkyl phosphites to N-tert-butylsulfinyl aldimines or ketimines occurs successfully at room temperature with potassium carbonate as base to afford α-amino- and α-alkyl-α-amino-N- (tert-butylsulfinyl)phosphonates in good to excel

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