13138-37-9

Usage

Chemical Properties

white to off-white crystalline powder

InChI:InChI=1/C5H14NO3P/c1-2-3-4-5(6)10(7,8)9/h5H,2-4,6H2,1H3,(H2,7,8,9)/p-1/t5-/m1/s1

Upstream product

• 110-62-3 pentanal 
• 4134-14-9 ethyl 2-(diethoxyphosphoryl)hexanoate 
• 60347-05-9 (1-pentylidenehydrazino-pentyl)-phosphonic acid diethyl ester 
• 25881-34-9 (1-benzylamino-pentyl)-phosphonic acid 
• 79014-52-1 1-Isocyanpentylphosphonsaeure-diethylester 
• 63459-06-3 N-benzyl-N-(butylidene)amine 
• 33439-85-9 1-acetylaminopentylphosphonic acid 
• 67398-29-2 diphenyl [(R,S)-1-(3-phenylthioureido)pentyl]phosphonate 
• 60347-13-9 dipentylidene-hydrazine 
• 77526-38-6 [1-(Dimethyl-hydrazono)-pentyl]-phosphonic acid diethyl ester 
• 13504-66-0 diethyl pentanoylphosphonate 
• 110-59-8 pentanonitrile 
• 77526-42-2 (1-amino-pentyl)-phosphonic acid diethyl ester 

Downstream Products

• 35045-93-3 1-N-Benzoylamino-pentylphosphonsaeure 
• 80088-88-6 [(R,S)-1-(benzyloxycarbonylamino)pentyl]phosphonic acid 
• 110-62-3 pentanal 
• 71-41-0 pentan-1-ol 
• 110-59-8 pentanonitrile 
• 34880-43-8 2-propylheptenal 
• 106019-45-8 benzyl hydrogen [(R,S)-1-(benzyloxycarbonylamino)pent-1-yl]phosphonate 
• 1181104-67-5 (2S)-2-{[(2S)-2-{[(R,S)-1-benzyloxycarbonylaminopentyl(benzyloxy)phosphoryl]oxy}propanoyl]amino}-3-methylbutanamide 
• 1181104-66-4 (2S)-2-[({[(R,S)-1-benzyloxycarbonylaminopentyl(benzyloxy)phosphoryl]oxy}acetyl)amino]-3-methylbutanamide 
• 1181104-63-1 methyl (2S)-2-{[(2S)-2-{[(R,S)-1-benzyloxycarbonylaminopentyl(benzyloxy)phosphoryl]oxy}propanoyl]amino}-3-methylbutanoate 
• 1181104-62-0 methyl (2S)-2-[({[(R,S)-1-benzyloxycarbonylaminopentyl(benzyloxy)phosphoryl]oxy}acetyl)amino]-3-methylbutanoate 
• 1043504-74-0 benzyl (2S)-2-{[(2S)-2-{[(R,S)-1-benzyloxycarbonylaminopentyl(benzyloxy)phosphoryl]oxy}propanoyl]amino}-3-methylbutanoate 
• 1043504-72-8 benzyl (2S)-2-[({[(R,S)-1-benzyloxycarbonylaminopentyl(benzyloxy)phosphoryl]oxy}acetyl)amino]-3-methylbutanoate 
• 1043504-64-8 (2S)-2-{[(R,S)-1-benzyloxycarbonylaminopentyl(benzyloxy)phosphoryl]oxy}propionamide 

Relevant academic research and scientific papers

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

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.

Efficient synthesis of phosphonodepsipeptides derived from norleucine

In the present work, we describe in detail an efficient solution synthesis of norleucine-derived phosphonopeptides mimicking the peptide sequences Nle-Gly(Ala) and Nle-Gly(Ala)-Val. The most efficient strategy involved use of the benzyl group. The synthesis was achieved through BOP-catalysed coupling of the monobenzyl ester of the N-Cbz-protected phosphonate derivative of norleucine with the hydroxyl moieties of derivatised l-lactic or glycolic acid. Subsequently, complete deprotection of the products was achieved in good yields by one-step Pd-catalysed hydrogenolysis. We also prepared the Fmoc-Nle-Ψ[PO(OH)O]-CH2-COOH synthon and demonstrated that this precursor is a suitable building block for the solid-phase synthesis of cysteine-containing phosphonopeptides.

Synthesis of norleucine-derived phosphonopeptides

The synthesis of norleucine-derived phosphonopeptides was achieved by BOP-catalyzed coupling of the monobenzyl ester of a N-CBz-protected phosphonate derivative of norleucine with hydroxyl moieties of derivatized lactic or glycolic acids. The complete deprotection of the product esters/carbamates was achieved in good yields by one-step Pd-catalyzed hydrogenolysis.

ORGANOPHOSPHORUS COMPOUNDS AS POTENTIAL FUNGICIDES. PART II. AMINOALKANE-, GUANIDINOALKANE-, AND THIOUREIDOALKANE-PHOSPHONIC ACIDS: PREPARATION, SPECTROSCOPY, AND FUNGICIDAL ACTIVITY

A range of α-amino-, ω-amino-, α-guanidino-, and ω-guanidinoalkanephosphonic acids has been prepared for the purpose of studying their spectroscopic features and fungicidal activity.In addition, α-thioureido-octanephosphonic acid and thioureylene-1,1-bis(1-octanephosphonic acid) were isolated during the preparation of α-guanidino-octanephosphonic acid. 31P, 1H, and 13C nmr spectral data which were obtained for solutions of the amino- and guanidino-compounds in D2O or D2O/D2SO4, and for the thioureido compounds in DMSO-d6, are discussed together with previouslyreported data for the aminophosphonic types.FAB mass spectrometry generally gives strong pseudomolecular ions + for the zwitterionic amino- and guanidino-compounds with relatively simple fragmentations.Fungicidal activity of the α-aminophosphonic acids was found to be greater than for the ω-amino compounds, with maximum activity at a chain length of three carbon atoms when used as a seed dressing for the control of Drechslera spp.Moderately good activity was shown by the thioureido compounds against a number of fungal organisms in vitro but the guanidino-compounds exhibited low activity.Key words: Organophosphorus; fungicides; aminophosphonic acids; guanidinophosphonic acids; NMR spectroscopy; FAB mass spectroscopy.

1-Aminoalkanephosphonic acids. Addition of diethyl phosphite to N-diisobutylaluminio-aldimines

A new route to 1-aminoalkanephosphonic acids starting from nitriles has been elaborated.The nitriles are reduced by Dibal-H into imine derivatives; addition with diethyl phosphite gives the corresponding 1-aminoalkanephosphonates.Hydrolysis of latter compounds gives the 1-aminoalkanephosphonic acids.

Enkephalin analogs and a process for the preparation thereof

The invention relates to new enkephalin analogues of the general formula (I), wherein Tyr, Gly and Phe represent L-tyrosyl, glycyl and L-phenylalanyl residue, respectively, X is glycyl residue or a D-α-aminocarboxylic acid residue with a lower alkyl, lowe