104944-25-4

Upstream product

• 119552-91-9 (R)-(+)-dibenzyl hydroxy(phenyl)methanephosphonate 
• 536739-07-8 diallyl (R)-α-hydroxybenzylphosphonate 
• 85185-11-1 diethyl [(R)-hydroxy(phenyl)methyl]phosphonate 
• 3277-27-8 diethyl benzoylphosphonate 
• 100-52-7 benzaldehyde 
• 741292-48-8 di-(1R,2S,5R)-menthyl benzoylphosphonate 
• 98-88-4 benzoyl chloride 
• 18406-56-9 Bis(trimethylsilyl) benzylphosphonate 
• 1499-19-0 benzylphosphonic dichloride 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 211134-57-5 (-)-di-[(1R,2S,5R)-menth-2-yl] (α-hydroxybenzyl)phosphonate 
• 211134-54-2 ((R)-Hydroxy-phenyl-methyl)-phosphonic acid bis-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester 
• 74038-34-9 diallyl benzylphosphonate 

Downstream Products

• 119552-91-9 (R)-(+)-dibenzyl hydroxy(phenyl)methanephosphonate 
• 104944-34-5 (R)-2-tert-Butoxycarbonylamino-propionic acid (R)-(bis-benzhydryloxy-phosphoryl)-phenyl-methyl ester 
• 104944-40-3 (R)-2-Amino-3-methyl-butyric acid (R)-phenyl-phosphono-methyl ester 
• 104944-39-0 (R)-2-Amino-propionic acid (R)-phenyl-phosphono-methyl ester 
• 104944-35-6 (R)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid (R)-(bis-benzhydryloxy-phosphoryl)-phenyl-methyl ester 
• 89865-26-9 (Hydroxy-phenyl-methyl)-phosphonic acid dibenzhydryl ester 

Relevant academic research and scientific papers

Double asymmetric induction as method for the synthesis of chiral organophosphorus compounds

New examples of multistereoselective syntheses of organophosphorus compounds are described.

Enantioselective reduction of ketophosphonates using adducts of chiral natural acids with sodium borohydride

A method for asymmetric reduction of α- and β-ketophosphonates using chiral complexes prepared from sodium borohydride and natural aminoacids or tartaric acids was developed. Reduction of α or β-ketophosphonates by these reagents led to formation of chiral (S)- or (R)- hydroxyphosphonates. Reduction of chiral di-(1R,2S,5R)-menthylketophosphonates by the chiral complexes NaBH4/(R,R)-proline or NaBH4/(R,R)-tartaric acid due to the double matched asymmetric induction resulted in increased stereoselectivity of the reaction and led to the formation of hydroxyphosphonates up to 90% ee or higher. Dimenthyl 2-hydroxy-3- chloropropylphosphonate was utilized as a chiron for the preparation of a number of biologically active compounds in multigram quantity. ARKAT-USA, Inc.

New method for the asymmetric reduction of ketophosphonates

Chiral reducing reactants were prepared from lithium, sodium, or tetrabutylammonium borohydrides and (S)- or (R)-tartaric acids. Copyright Taylor & Francis Group, LLC.

Synthesis of optically active hydroxyphosphonates

The reduction of dimenthyl ketophosphonates with sodium borohydride involves asymmetric induction at the a-carbon atom, resulting in a small excess of the (R)-enantiomer of the a-hydroxyphosphonate formed. A higher ee purity was achieved if the reduction

Organic catalysis of phospha-aldol condensation

Phospha-aldol reaction of dialkylphosphites with carbonyl compounds is catalyzed by cinchonine alkaloids and thier modified derivatives to give optically active hydroxyphosphonates. The use of diastereomeric pairs of alkaloids allowed obtaining both optic

New method for the asymmetric hydroboration of ketophosphonates and the synthesis of phospho-carnitine

The reduction of α- or β-ketophosphonates with a chiral reactant 1, prepared from sodium borohydride and (R)- or (S)-tartaric acids, led to the formation of both (S)- and (R)-α- or β-hydroxyphosphonates in high yields. The stereoselectivity of the reactio

Enantioselective reduction of ketophosphonates using chiral acid adducts with sodium borohydride

A method for asymmetric reduction of α-and β-ketophosphonates using a chiral complex prepared from sodium borohydride and D-or L-tartaric acid is developed. Reduction of α-or β-ketophosphonates by these reagents led to formation of corresponding (S)-or (R

Chiral, non-racemic α-hydroxyphosphonates and phosphonic acids via stereoselective hydroxylation of diallyl benzylphosphonates

Chiral, non-racemic α-hydroxyphosphonates have been prepared in high enantiomeric excess (96-98% ee), via stereoselective oxaziridine-mediated hydroxylation of diallyl benzylphosphonates. The enantiomeric purity and absolute configuration of the α-hydroxy

Asymmetric synthesis of α-substituted alkylphosphonates based on symmetrical dialkyl phosphites

Chiral C2-symmetrical dialkyl phosphites and C3-symmetrical trialkyl phosphites, derived from (-)-borneol, (-)-menthol, and 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, were studied as the starting reagents for the preparation of chiral organophosphorus compounds. The reactions of C2-symmetrical dialkyl phosphites and C3-symmetrical trialkyl phosphites with aldehydes and amines or aldehydes are accompanied by asymmetrical induction at the α-carbon atom to yield optically active α-aminoalkylphosphonates or α-hydroxyalkylphosphonates, respectively. The stereoselectivity of the reaction depends on the structure of the starting compounds and the reaction conditions.

Chiral symmetric phosphoric acid esters as sources of optically active organophosphorus compounds

Chiral symmetric di- and trialkylphosphites, derivatives of (-)-borneol, (-)-menthol and (-)-1,2:5,6-di-Oisopropylidene-α-D-glucofuranose, were studied as starting reagents for the preparation of chiral organophosphorus compounds. The reaction occurs by a