211134-55-3

Upstream product

• 78-84-2 isobutyraldehyde 
• 943975-09-5 di-[(1R,2S,5R)-(-)-menth-2-yl] 2-methylpropionylphosphonate 
• 2216-51-5 (-)-menthol 
• 945652-58-4 di-[(1R,2S,5R)-(-)-menth-2-yl] hydroxy-(isopropyl)methylphosphonate 
• 211183-18-5 hydrogen di[(1R,2S,5R)-menthyl] phosphite 

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.

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.

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