107389-05-9

Upstream product

• 645-45-4 hydrocinnamic acid chloride 
• 122-52-1 triethyl phosphite 
• 81364-33-2 diethyl (1-hydroxy-3-phenylpropyl)phosphonate 
• 78-40-0 triethyl phosphate 
• 104-53-0 3-phenyl-propionaldehyde 

Downstream Products

• 141543-07-9 (1-Hydroxy-1-nitromethyl-3-phenyl-propyl)-phosphonic acid diethyl ester 
• 107389-07-1 (S)-1-[(S)-2-(3-Phenyl-propionylamino)-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 107389-06-0 (S)-1-{(S)-2-[(E)-1-(Diethoxy-phosphoryl)-3-phenyl-propenylamino]-propionyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 107389-08-2 (S)-1-{(S)-2-[(R)-1-(Diethoxy-phosphoryl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 107389-08-2 (S)-1-{(S)-2-[(S)-1-(Diethoxy-phosphoryl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 1083-30-3 dihydrochalcone 
• 107389-09-3 (S)-1-[(S)-2-((R)-3-Phenyl-1-phosphono-propylamino)-propionyl]-pyrrolidine-2-carboxylic acid 
• 107389-09-3 (S)-1-[(S)-2-((S)-3-Phenyl-1-phosphono-propylamino)-propionyl]-pyrrolidine-2-carboxylic acid 
• 1262726-78-2 C₁₃H₂₁N₂O₃P 
• 154118-57-7 diethyl 1-nitro-3-phenylpropylphosphonate 
• 1445598-25-3 diethyl 3-nitro-1-phenyl-5-(phenylsulfonyl)pentan-3-ylphosphonate 

Relevant academic research and scientific papers

Reactions of acyl tributylphosphonium chlorides and dialkyl acylphosphonates with Grignard and organolithium reagents

Ketones and esters (4) were effectively prepared by reaction of Grignard reagents with acyl tributylphosphonium chlorides (2), diethyl acylphosphonates (5), or diisopropyl acylphosphonate (6) derived from acid chlorides and chloroformates (1). Although by the method with 2, 4 is prepared in one-pot operation from 1 and generally in a higher yield, the method with 5 or 6 proved to compensate for the synthesis of 4 with 2 in some respects. The reactivities of 2, 5, and 6 as electrophiles were also evaluated by comparing their reduction potential with those of acid chlorides.

Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates

A carbene-catalyzed enantioselective [4+2] cycloaddition reaction between α,β-unsaturated aldehydes and α-ketophosphonates is developed. The reaction affords chiral 2-pyranylphosphonates with excellent enantioselectivities. The optically enriched phosphonate products bear multiple functional groups, including unsaturated lactone and phosphonate moieties that often lead to unique bio-activities. Preliminary studies show that the products from our reactions exhibit anti-bacterial (X. oryzae pv. oryzae) and anti-viral (Tobacco Mosaic Virus) activities for potential use in plant protection.

Catalytic Aldol-Cyclization Cascade of 3-Isothiocyanato Oxindoles with α-Ketophosphonates for the Enantioselective Synthesis of β-Amino-α-hydroxyphosphonates

A cascade aldol-cyclization reaction between 3-isothiocyanato oxindoles and α-ketophosphonates has been developed for the synthesis of β-amino-α-hydroxyphosphonate derivatives. Catalyzed by a quinine-based tertiary amino-thiourea derivative, this reaction

Enantioselective synthesis of α-amino-γ-sulfonyl phosphonates with a tetrasubstituted chiral α-carbon via quinine-squaramide-catalyzed michael addition of nitrophosphonates to vinyl sulfones

α-Nitro-γ-sulfonyl phosphonates with a key tetrasubstituted chiral α-carbon center have been synthesized for the first time in high yield and enantioselectivity through a quinine-squaramide-catalyzed conjugate addition of α-nitro phosphonates to aryl vinyl sulfones. Representative examples presented here for the transformation of nitrosulfonyl phosphonates to aminosulfonyl phosphonates, alkylation at the α-position of the sulfonyl group followed by desulfonation and scale-up of the conjugate addition highlight the practical applications of the methodology. Copyright

Non-hydrolysable analogues of inorganic pyrophosphate as inhibitors of hepatitis C virus RNA-dependent RNA-polymerase

Inorganic pyrophosphate (PPi) is the product of the polymerization reaction catalyzed by DNA-and RNA-polymerases. A number of novel non-hydrolsable PPi analogues was synthesized; some of them inhibited the polymerization reaction catalyzed by hepatitis C virus RNA-dependent RNA-polymerase (NS5B). A new pharmacophore based on a non-hydrolysable methylenediphosphonate backbone has been developed. The structure-activity relationship analysis of 12 bisphosphonates is presented and the structural features crucial for NS5B polymerase activity inhibition are stated. Pleiades Publishing, Ltd., 2012.

Room-temperature alternative to the arbuzov reaction: The reductive deoxygenation of Acyl phosphonates

The reductive deoxygenation of acyl phosphonates using a Wolff-Kishner-like sequence is described. This transformation allows direct access to alkyl phosphonates from acyl phosphonates at room temperature. The method can be combined with acyl phosphonate synthesis into a one pot, four-step procedure for the conversion of carboxylic acids into alkyl phosphonates. The methodology works well for a variety of aliphatic acids and shows a functional group tolerance similar to that of other hydrazone-forming reactions.

A convenient and mild procedure for the preparation of α-keto phosphonates of 1-hydroxyphosphonates under solvent-free conditions using microwave

The Reactions of 1-hydroxyphosphonates on the alumina-supported CrO3 are accelerated by microwave irradiation under solvent-free conditions to afford a high yielding synthesis of α-keto phosphonates.

Surface-mediated solid-phase reactions: The preparation of acyl phosphonates by oxidation of 1-hydroxyphosphonates on the solid surface

Alumina-supported CrO3, under solvent-free conditions, was found to be an efficient oxidizing reagent for the preparation of acyl phosphonates from 1-hydroxyphosphonates. This method is an easy, rapid, and high-yielding reaction for the prepara