110548-52-2

Upstream product

• 71864-40-9 carbamic acid N-[(dimethoxyphosphinyl)phenylmethyl] 1,1-dimethylethyl ester 
• 100-52-7 benzaldehyde 
• 868-85-9 Dimethyl phosphite 
• 59191-30-9 O,O-dimethyl {[(benzyloxy)carbonyl]amino}(phenyl)methylphosphonate 
• 96721-65-2 C₁₆H₁₈NO₃P 
• 92-29-5 hydrobenzamide 
• 681035-60-9 O,O-dimethyl (R)-{[(1R)-2-hydroxy-1-phenylethyl]amino}(phenyl)methylphosphonate 
• 681035-55-2 O,O-dimethyl (R)-{[(1R)-2-hydroxy-1-phenylethyl]amino}(phenyl)methylphosphonothioate 
• 74879-43-9 (R)-N-benzylidene-2-hydroxy-1-phenylethylamine 

Downstream Products

• 1347739-89-2 O,O-dimethyl [2-(4,6-dimethoxypyrimidin-2-yloxy)phenoxyamino](phenyl)methylphosphonate 
• 1396320-40-3 O,O'-dimethyl-α-(thiazolo[5,4-b]pyridin-2-yl)amino(phenylmethyl)phosphonate 
• 37714-05-9 (R)-1-amino-1-phenylmethylphosphonic acid 

Relevant academic research and scientific papers

Synthesis and cytotoxicity of O,O′-dialkyl {[2-(substituted phenoxy)acetamido](substituted phenyl)methyl}phosphonates

A series of O,O′-dialkyl {[2-(substituted phenoxy)acetamido] (substituted phenyl)methyl}phosphonates was synthesized and their cytotoxic activities were tested against various human tumor cell lines. Some compounds (5q, 5r, 5s, 5w, 5x and 5y) showed relatively high cytotoxicity. Especially, compounds 5x and 5q exhibited the best cytotoxicity against KB and CNE2 cells with IC50 7.1 and 11.4 μM, respectively. Their inhibitory activities against KB and CNE2 cells were even higher than that of fluorouracil.

Synthesis and biological evaluation of novel phosphonates derivatives of as potential antitumor agents

A series of dialkyl [2-(4,6-dimethoxypyrimidin-2-yloxy)benzamido](aryl) methylphosphonates derivatives were designed and synthesized. All the new compounds were identified by elemental analysis, IR, 1H NMR, 31P NMR, and MS. Their antitumor activity against KB and CNE1 cells was examined. Some of the compounds showed potential antitumor activity, which provided some hints for further study of structure modification. In particular, the compounds 6i and 6j displayed more potent cytotoxic activities against KB in comparison with 5-FU. Copyright Taylor & Francis Group, LLC.

Synthesis of an optically active al(salalen) complex and its application to catalytic hydrophosphonylation of aldehydes and aldimines

Optically active aluminum(salalen) complex 2 was newly synthesized in a modular synthetic manner, and it was found to serve as an efficient catalyst for hydrophosphonylation of aldehydes and aldimines, giving the corresponding α-hydroxy and α-amino phosph

X=Y=ZH systems as potential 1,3-dipoles. Part 62:1 1,3-Dipolar cycloaddition reactions of metallo-azomethine ylides derived from α-iminophosphonates

Metallo-azomethine ylides, generated from iminophosphonates in combination with LiBr or AgOAc and bases Et3N, DBU, t-butyl tetramethylguanidine(BTMG) undergo cycloaddition to give dialkyl pyrrolidine-2-phosphonates along with the corresponding

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 mild and highly efficient protocol for the one-pot synthesis of primary α-amino phosphonates under solvent-free conditions

Under solvent-free reaction conditions and in the presence of solid LiClO4 a novel and mild protocol for the one-pot, three-component synthesis of primary α-amino phosphonates from an aldehyde, hexamethyldisilazane and a trialkyl phosphite is described giving high yields and having short reaction times. The same products are obtained in very low yields, when the three-component reaction is carried out under microwave irradiation and in the absence of solid LiClO4. Examples of some prepared 1-aryl-N,N′-bis(arylidene)methanediamines are also described.

The synthesis of N-(β-triphenylgermanyl)-propionyl-α-amino-benzylphosphonates

A series of N-(β-triphenylgermanyl)propionyl-α-amino-benzylphosphonates was synthesized by reaction of β-triphenylgermanyl propionic acid with α-aminophosphonates under very mild conditions. The structures of products were determined by 1H NMR,

Simple and improved preparation α-aminophosphonic acid derivatives, key building blocks of phosphonopeptides

Strecker-type reaction of an aldehyde, ammonium acetate and diethyl phosphite in ethanol afforded the corresponding diethyl α-aminophosphonate, a key building block of the biologically interesting phosphonopeptides, in moderate to good yield.