18108-24-2Relevant articles and documents
Enzymes in organic chemistry. Part 9: Chemo-enzymatic synthesis of phosphonic acid analogues of L-valine, L-leucine, L-isoleucine, L-methionine and L-α-aminobutyric acid of high enantiomeric excess
Hammerschmidt, Friedrich,Wuggenig, Frank
, p. 1709 - 1721 (1999)
Diisopropyl α-chloroacetoxyphosphonates derived from propanal, isobutanl, 3-methylmercaptopropanal, 3-methylbutanal and (S)-2-methylbutanal were resolved by enzyme-catalysed hydrolysis. Lipases preferentially hydrolysed the (S)-esters and protease Chirazyme P-2 the (R)-esters. Replacing the isopropyl groups by t-butyl groups reduced the reaction rate; replacing them by a 2,2-dimethylpropane-1,3-diyl group increased the reaction rate. (S)-α-Hydroxyphosphonates (ee 92-99%), obtained with the protease except one, were transformed into phosphonic acid analogues of L-valine, L- leucine, L-isoleucine, L-methionine and L-α-aminobutyric acid. Their enantiomeric purity was determined by HPLC on a chiral stationary phase after derivatisation at nitrogen.
Conversion of nitriles to 1-aminophosphonic acids and preparation of phosphahomocysteines of high enantiomeric excess
Qian, Renzhe,Horak, Jeannie,Hammerschmidt, Friedrich
, p. 737 - 744 (2017/06/05)
A variety of nitriles was reduced to diisobutylaluminum salts of aldimines, to which diisopropyl phosphite was added. The corresponding 1-aminophosphonates were either deprotected to give racemic 1-aminophosphonic acids or reacted with Boc2O to yield N-Boc-protected 1-aminophosphonates. The enantiomers of 2-benzylthio-1-(t-butoxycarbonylamino)propylphosphonate were obtained from the racemate by chiral HPLC and converted to phosphonic acid analogs of (R)- and (S)-homocysteine, (R)- and (S)-2-aminobutyric acid and (S)-methionine, all of ee >97% as determined by chiral HPLC.
Tritylamine (triphenylmethylamine) in organic synthesis; III. The synthesis of 1-aminoalkylphosphonic acids in the reaction of N-(triphenylmethyl) alkanimines with phosphorus trichloride in acetic acid or with phosphonic (phosphorous) acid in acetic anhydride
Goldeman, Waldemar,Soroka, Miroslaw
experimental part, p. 360 - 369 (2011/02/27)
The reaction of phosphorus trichloride in acetic acid or phosphonic (phosphorous) acid in acetic anhydride, with N-(triphenylmethyl)alkanimines gives 1-acetylaminoalkylphosphonic acids 1a-j, which after hydrolysis give 1-aminoalkylphosphonic acids 2a-j in good yields. ARKAT USA, Inc.
