945652-61-9

Upstream product

• 2216-51-5 (-)-menthol 
• 900537-08-8 di(1R,2S,5R)-menthyl 2-keto-3-chloropropylphosphonate 
• 900537-07-7 di(1R,2S,5R)-menthyl methylphosphonate 
• 900537-05-5 bis[(1R,2S,5R)-menthyl] ((S)-3-chloro-2-hydroxypropyl)phosphonate 

Downstream Products

• 945652-64-2 di(1R,2S,5R)-menthyl (2R)-2-hydroxy-3-azidopropylphosphonate 
• 945652-62-0 bis[(1R,2S,5R)-menthyl] [(2R)-3-(dibenzylamino)-2-hydroxypropyl]phosphonate 

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.

Di(1R,2S,5R)-menthyl 2-hydroxy-3-chloropropylphosphonate as a useful chiral synthon for the preparation of enantiomerically pure phosphonic acids

Stereochemically pure di(1R,2S,5R)-menthyl (S)- and (R)-2-hydroxy-3- chloropropylphosphonates were synthesized by reaction of di(1R,2S,5R)-menthyl ketophosphonate with chiral complexes prepared from sodium borohydride and (R,R)-(+)-tartaric acid or with (

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.