889103-61-1

Upstream product

• 100-52-7 benzaldehyde 
• 211183-18-5 hydrogen di[(1R,2S,5R)-menthyl] phosphite 
• 78392-42-4 tris-[(1R,2S,5R)-menth-2-yl]phosphite 
• 741292-48-8 di-(1R,2S,5R)-menthyl benzoylphosphonate 
• 2216-51-5 (-)-menthol 
• 105449-76-1 di(1R,2S,5R)-menthyl phosphorochloridite 
• 98-88-4 benzoyl chloride 
• 889103-63-3 di-(1R,2S,5R)-menthyl α-hydroxybenzylphosphonate 

Downstream Products

• 104944-23-2 (-)-(S)-1-phenyl-1-hydroxymethylphosphonic acid 

Relevant academic research and scientific papers

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.

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

New methods and strategies for asymmetric synthesis of organophosphorus compounds

New methods for the asymmetric synthesis of organophosphorus compounds were developed and applied for the preparation of a number of biologically important enantiomerically pure products. Copyright Taylor & Francis Group, LLC.

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.

Efficient method for the asymmetric reduction of α- and β-ketophosphonates

An efficient and versatile method for the asymmetric reduction of α- and β-ketophosphonates using chiral reactant derived from sodium borohydride and l-(+)- or d-(-)-tartaric acid is developed. The methodology was used for the preparation of a number of biologically interesting enantiomerically pure products: including 2,3-epoxypropylphosphonate 11, 2-hydroxy-3-aminopropylphosphonic acid 14 (phospho-GABOB), phospho-carnitine 19, and others in multigram scale.

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

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