94776-38-2

Upstream product

• 1795-31-9 tris(trimethylsilyl) phosphite 
• 104173-32-2 (R)-4-(Diphenoxy-phosphoryl)-2-isopropyl-oxazolidine-3-carboxylic acid methyl ester 
• 121330-03-8 (R)-(-)-<1-Azido-2-(benzyloxy)ethyl>phosphonsaeure-dimethylester 
• 98820-95-2 [(R)-1-((S)-2-Amino-propionylamino)-2-hydroxy-ethyl]-phosphonic acid 
• 94776-37-1 C₃₄H₂₈NO₁₁P 

Relevant academic research and scientific papers

Enzymes in organic chemistry. Part 10:1 Chemo-enzymatic synthesis of L- phosphaserine and L-phosphaisoserine and enantioseparation of amino- hydroxyethylphosphonic acids by non-aqueous capillary electrophoresis with quinine carbamate as chiral ion pair agent

Diisopropyl 2-azido-1-acetoxyethylphosphonate (±)-7 was hydrolysed with high enantioselectivity by lipase SP 524 to give α-hydroxyphosphonate (S)-(- )-6 and ester (R)-(-)-7, which was saponified to give (R)-(+)-6. The two α- hydroxyphosphonates (R)- and (S)-6 were transformed into l-phosphaisoserine and L-phosphaserine, respectively. Their enantiomeric excesses were determined to be 97% by HPLC on an chiral stationary phase. A mixture of all four stereoisomeric amino-hydroxyethylphosphonic acids can be separated by non-aqueous capillary electrophoresis with quinine carbamate as the chiral ion pair agent applying the partial filling technique. (C) 2000 Elsevier Science Ltd.

Absolute Configuration of (2-Amino-1-hydroxyethyl)phosphonic Acid from Acanthamoeba castellanii (Neff) - Preparation of Phosphonic Acid Analogues of (+)- and (-)-Serine

Dimethyl phosphonate was derivatised with dimeric lactol (+)-8 to give the chromatographically separable diastereomers 9 and 10.By removing the chiral auxiliary under acidic conditions, the enantiomeric phosphonates

133. Nucleophilic Additions to N-Glycosylnitrones. Part IV. Asymmetric Synthesis of N-Hydroxy-α-aminophosphonic and α-Aminophosphonic Acids

The addition of phosphite anions and of tris(trimethylsilyl)phosphite (P(OSiMe3)3) to N-glycosyl-C-aryl-nitrones was examined.While these nitrones proved inert towards the phosphite anions, they reacted with P(OSiMe3)3 under catalysis by Lewis acids.Thus,

Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid

Phosphonodipeptides and phosphonooligopeptides based on L- and D-(1-aminoethyl)phosphonic acids L-Ala(P) and D-Ala(P) and (aminomethyl)phosphonic acid Gly(P) at the acid terminus have been synthesized and investigated as antibacterial agents, which owe their activity to the inhibition of bacterial cell-wall biosynthesis. A method for large-scale synthesis of the potent antibacterial agent L-Ala-L-Ala(P) (1,Alafosfalin) is described. Structure-activity relationships in the dipeptide series have been studied by systematic variation of structure 1. L stereochemistry is generally required for both components. Changes in the L-Ala(P) moiety mostly lead to loss of antibacterial activity, but the phosphonate analogues of L-phenylalanines, L-Phe(P), and L-serine, L-Ser(P), give rise to weakly active L-Ala-L-Phe(P) and L-Ala-L-Ser(P). Replacement of L-Ala in 1 by common and are amino acids can give rise to more potent in vitro antibacterials such as L-Nva-L-Ala(P). Synthetic variation of these more potent dipeptides leads to decreased activity. Phosphonooligopeptides such as (L-Ala)2-L-Ala(P) have a broader in vitro antibacterial spectrum than their phosphonodipeptide precursor, but this is not expressed in vivo, presumably due to rapid metabolism to 1. Stabilized compounds such as Sar-L-Nva-L-Nva-L-Ala(P) have been developed that are more potent in vivo and have a broader in vivo antibacterial spectrum than the parent phosphonodipeptide.