86552-40-1

Upstream product

• 100-42-5 styrene 
• 103-63-9 1-phenyl-2-bromoethane 
• 86552-39-8 ethyl 2-phenylethyl-H-phosphinate 
• 90878-19-6 phenethylmagnesium chloride 
• 6303-21-5 hypophosphorous acid 
• 7647-01-0 hydrogenchloride 
• 589-57-1 diethyl phosphorylchloridite 

Downstream Products

• 200698-30-2 2,4-di(benzyloxycarbonyl)-butyl(phenethyl)phosphinic acid 
• 86552-41-2 benzyl (2-phenylethyl)phosphinate 
• 439800-08-5 [(S)-2-Benzyl-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propyl]-phenethyl-phosphinic acid 
• 439800-07-4 [(R)-2-Benzyl-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propyl]-phenethyl-phosphinic acid 
• 1189962-84-2 (1-(benzyloxycarbonylamino)-3-methylbutyl)(2-phenylethyl)phosphinic acid 
• 1189936-04-6 (1-(benzyloxycarbonylamino)-2-methylpropyl)(2-phenylethyl)phosphinic acid 
• 1330527-25-7 (1-(benzyloxycarbonylamino)propyl)(2-phenylethyl)phosphinic acid 

Relevant academic research and scientific papers

AMINOPEPTIDASE A INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME

The present invention relates to a novel compound, to a composition comprising the same, to methods for preparing the compound, and the use of this compound in therapy. In particular, the present invention relates to compound that is useful in the treatment and prevention of primary and secondary arterial hypertension, ictus, myocardial ischaemia, cardiac and renal insufficiency, myocardial infarction, peripheral vascular disease, diabetic proteinuria, Syndrome X and glaucoma.

Structure Property Relationships of Carboxylic Acid Isosteres

The replacement of a carboxylic acid with a surrogate structure, or (bio)-isostere, is a classical strategy in medicinal chemistry. The general underlying principle is that by maintaining the features of the carboxylic acid critical for biological activity, but appropriately modifying the physicochemical properties, improved analogs may result. In this context, a systematic assessment of the physicochemical properties of carboxylic acid isosteres would be desirable to enable more informed decisions of potential replacements to be used for analog design. Herein we report the structure-property relationships (SPR) of 35 phenylpropionic acid derivatives, in which the carboxylic acid moiety is replaced with a series of known isosteres. The data set generated provides an assessment of the relative impact on the physicochemical properties that these replacements may have compared to the carboxylic acid analog. As such, this study presents a framework for how to rationally apply isosteric replacements of the carboxylic acid functional group.

Method for the production of alkylphosphonic acids, esters, and salts by oxidizing alkylphosphonous acids, and use thereof

The invention relates to a method for producing monocarboxy-functionalized dialkylphosphinic acids, esters, and salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester (II) thereof, and b) the obtained alkylphosphonous acid, the salt or ester (II) thereof is reacted with an oxidizing agent or with an oxidizing agent and water or with oxygen and water in the presence of a catalyst B to obtain the alkylphosphonic acid derivative (III), wherein R1, R2, R3, R4 are identical or different from each other and independently represent, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, X and Y are identical or different from each other and independently represent H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogenous base, and catalysts A and B are transition metals and/or transition metal compounds and/or catalyst systems composed of a transition metal and/or a transition metal compound and at least one ligand.

Amidoalkylation of hydrophosphoryl compounds

A new mild procedure of the amidoalkylation of hydrophosphoryl compounds in a mixture of acetic anhydride and acetyl chloride was developed as a convenient method of constructing the a-aminophosphoryl fragment of the pseudo-a,a'-dipeptide molecule. The reaction intermediates N,N'-benzylidene- and N,N'-alkylidenebiscarbamates were detected, isolated, and identified. The report presents the results of studying the direct interaction of hydrophosphoryl compounds previously synthesized with biscarbamates in acetic anhydride and other solvents, the influence of the structure of phosphorus component and biscarbamate, and the effect of acid catalysis on the course of this two-component reaction. A new version of the mechanism of the three-component reaction of amidoalkylation of hydrophosphoryl compounds is suggested: it is regarded as a multistage process involving the stage of biscarbamate formation followed by the stage of Arbuzov-type reaction with the intermediate formation of acyliminium cation and P-OAc derivative with trivalent phosphorus. Pleiades Publishing, Ltd., 2011.

Reactions of elemental phoshorus and phosphine with electrophiles in superbasic systems: XIX. Formation of the C-P bond with participation of elemental phosphorus under microwave assistance

Microwave irradiation facilitates phosphorylation of aryl methyl chlorides and styrene with red phosphorus in the presence of strong bases and increases the yield of the main products, tertiary phosphine oxides. Nauka/Interperiodica 2007.

Recent advances in phosphorus-carbon bond formation: Synthesis of H-phosphinic acid derivatives from hypophosphorous compounds

This account summarizes the research conducted in our laboratory over the past five years. New methodologies were devised for the formation of P-C bonds with a focus on the reactions of hypophosphorous acid derivatives. Three types of reactions have been developed: palladium-catalyzed cross-coupling, room-temperature radical addition, and palladium-catalyzed addition. Our results are summarized in each of these areas and include some of our most recent data. (1) Our palladium-catalyzed cross-coupling has been extended to the direct coupling of alkyl phosphinates with a variety of aryl, heteroaryl, and even alkenyl electrophiles. (2) The addition of sodium hypophosphite under radical conditions is extended from alkenes to alkynes. (3) The catalytic addition of hypophosphorous compounds using palladium catalysts (hydrophosphinylation) is also discussed.

Environmentally benign synthesis of H-phosphinic acids using a water-tolerant, recyclable polymer-supported catalyst

(Chemical Equation Presented) A reusable polymer-supported hydrophosphinylation catalyst is described for the preparation of H-phosphinic acids. The polystyrene-based ligand is prepared in one step from commercially available compounds. The polymeric catalyst generally gives good yields for a variety of substrates and is water- and air-tolerant, although the scope of alkenes and alkynes which can be employed is somewhat narrower than with our original xantphos/Pd2dba3 catalyst.

Prodrugs of NAALAdase inhibitors

The present invention relates to prodrugs of NAALADase inhibitors, pharmaceutical compositions comprising the same, and methods of using the same to treat glutamate abnormalities and prostate diseases.

Enantioselective synthesis of phosphinyl peptidomimetics via an asymmetric Michael reaction of phosphonic acids with acrylate derivatives

Asymmetric Michael reaction of phosphinic or aminophosphinic acids with acrylate derivatives afforded phosphinyl dipeptidomimetics in excellent yields (>90 percent). Chiral induction of substituents at the α-position of acrylate derivatives of Evans oxazolidinone type auxiliaries was obtained in moderate to excellent diastereomeric and enantiomeric excesses (50-98 percent). Pure diastereomers and enantiomers of phosphinyl dipeptidomimetics 16-19 were also successfully separated by HPLC.