741292-51-3

Upstream product

• 78392-42-4 tris-[(1R,2S,5R)-menth-2-yl]phosphite 
• 135-02-4 ortho-anisaldehyde 
• 211183-18-5 hydrogen di[(1R,2S,5R)-menthyl] phosphite 
• 741292-49-9 di-[(1R,2S,5R)-(-)-menth-2-yl] 2-methoxybenzoylphosphonate 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 945652-56-2 di-[(1R,2S,5R)-(-)-menth-2-yl] hydroxy-(2-methoxyphenyl)methylphosphonate 

Downstream Products

• 741292-53-5 (+)-(R)-1-(o-methoxyphenyl)-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.

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

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

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.