17105-64-5

Upstream product

• 104-81-4 4-Methylbenzyl bromide 
• 121-45-9 phosphorous acid trimethyl ester 
• 104-82-5 4-Methylbenzyl chloride 
• 868-85-9 Dimethyl phosphite 
• 270921-38-5 (4-methylphenyl)methyl carbonate 
• 589-18-4 4-Methylbenzyl alcohol 

Downstream Products

• 174969-95-0 ethyl 4-(dimethylphosphonomethyl)-D-phenylalaninate 
• 174969-91-6 ethyl 4-(dimethylphosphonomethyl)-D,L-phenylalaninate 
• 174969-92-7 4-(dimethylphosphonomethyl)-L-phenylalanine 
• 174969-99-4 2-(Benzhydrylidene-amino)-3-[4-(dimethoxy-phosphorylmethyl)-phenyl]-propionic acid ethyl ester 
• 140866-78-0 (4-bromo-methylbenzyl)phosphonic acid dimethyl ester 
• 175445-88-2 3-[4-(Dimethoxy-phosphorylmethyl)-phenyl]-2-methyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester 
• 175445-90-6 methyl α-methyl-4-(dimethylphosphonomethyl)-D,L-phenylalaninate 

Relevant academic research and scientific papers

Tetrahydroquinolinyl phosphinamidates and phosphonamidates enhancing tolerance towards drought stress in crops via interaction with ABA receptor proteins

New phosphorous-containing lead structures against drought stress in crops interacting with RCAR/(PYR/PYL) receptor proteins were identified starting from in-depth SAR studies of related sulfonamide lead structures and protein docking studies. A converging 6-step synthesis via phosphinic chlorides and phosphono chloridates as key intermediates afforded envisaged tetrahydroquinolinyl phosphinamidates and phosphonamidates. Whilst tetrahydroquinolinyl phosphonamidates 13a,b exhibited low to moderate target affinities, the corresponding tetrahydroquinolinyl phosphinamidates 12a,b revealed confirmed strong affinities for RCAR/ (PYR/PYL) receptor proteins in Arabidopsis thaliana on the same level as essential plant hormone abscisic acid (ABA) combined with promising efficacy against drought stress in vivo (broad-acre crops wheat and canola).

SUBSTITUTED OXOTETRAHYDROQUINOLINYLPHOSPHINIC ACID AND PHOSPHINIC ACID AMIDES OR SALTS THEREOF AND USE THEREOF TO INCREASE STRESS TOLERANCE IN PLANTS

The invention relates to substituted oxotetrahydroquinolinylphosphin- and -phosphonamides of the general formula (I) and salts thereof where the radicals of the formula (I) are each as defined in the description for enhancing stress tolerance in plants to abiotic stress, and for enhancing plant growth and/or for increasing plant yield.

Palladium-catalyzed benzylic substitution of benzyl carbonates with phosphorus nucleophiles

A wide range of benzyl carbonates reacted with dimethyl phosphonate or diphenylphosphine oxide in the presence of the palladium catalyst, [Pd(η3-allyl)Cl]2DPEphos, to give dimethyl benzylphosphonates and benzyldiphenylphosphine oxides in high yields. The catalytic phosphonylation was applied to the one-pot synthesis of alkenes from the benzyl esters.

Alkyl phosphonate preparing method

The invention provides an alkyl phosphonate preparing method. The method comprises: performing an Arbuzov reaction on compound A and compound B in a continuous reaction apparatus, and continuously discharging the product obtained from the reaction from the continuous reaction apparatus during the reaction procedure, to obtain alkyl phosphonate. The reaction temperature in the reaction procedure is T1; either of compound A and compound B having a lower boiling point has a boiling point at a standard atmosphere pressure to be T2; T1 is higher than T2 by 10-40 DEG C; and the reaction pressure in the reaction procedure is 0.5-2.0 MPa. The preparing method in the invention may use halohydrocarbon having large steric hindrance and lower polarizability of carbon-halogen bond as compound A, thereby effectively expanding a selection range of substrate, and correspondingly expanding the types of alkyl phosphonate prepared by using the Arbuzov reaction.

New synthesis of D,L-Fmoc protected 4-phosphonomethylphenylalanine derivatives and their enzymatic resolution

A new synthesis of N-Fmoc-4-phosphonomethyl-D,L-phenylalanine protected under di-tert-butyl or dimethyl phosphonate forms (Fmoc-Pmp(OR)2), suitable for solid phase peptide synthesis is described. Resolution of these hydrolytically stable analogs of O-phosphotyrosine was tried either by fractional recrystallization of diastereoisomeric salts or by using the subtilisin Carlsberg esterase. Only the enzymatic resolution of ethyl 4-[(dimethylphosphono)methyl]-D,L-phenylalaninate succeeded. These results are discussed by comparison with the literature data. The L and D amino acids were used to prepare separately, through solid-phase peptide synthesis, followed by deprotection of dimethylphosphonate group by trimethylsilyliodide (TMSI) in acetonitrile, the L and D isomers of Glu-Asp-Val-Pmp-Glu-Asn-Leu-His-Thr, a peptide corresponding to a potentially phosphorylated site of the phosphatase PTP 1C.

Synthesis of constrained 4-(phosphonomethyl)phenylalanine derivatives as hydrolytically stable analogs of O-phosphotyrosine

In order to elucidate the role of protein tyrosine phosphorylation involved in various intracellular signaling pathways, peptides containing O-phosphotyrosine have been developed. However, in order to improve the stability of the phosphorylation amino acid, we have designed some years ago a hydrolytically stable analogue,the 4-(phosphonomethyl)phenylalanine (Pmp). Introduced in peptide sequences, this residue, which is resistant to phosphatase action, was shown also able to inhibit substrate recognition by protein targets. With the aim to design peptidomimetics endowed with improved affinity and selectivity, we report in this study the synthesis of five new sterically hindered amino acids derived from Pmp. These modifications include α-methyl, β-methyl, β,β-dimethyl substitutions, α,β-cyclization of Pmp and methyl substitution on the phosphonomethyl group of Pmp.