1181104-51-7

Basic information

• Product Name: methyl hydrogen [(R,S)-1-(benzyloxycarbonylamino)pent-1-yl]phosphonate
• Synonyms: methyl hydrogen [(R,S)-1-(benzyloxycarbonylamino)pent-1-yl]phosphonate
• CAS NO: 1181104-51-7
• Molecular Weight: 315.306
• Mol File: 1181104-51-7.mol

Chemical Properties

• CAS DataBase Reference: methyl hydrogen [(R,S)-1-(benzyloxycarbonylamino)pent-1-yl]phosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl hydrogen [(R,S)-1-(benzyloxycarbonylamino)pent-1-yl]phosphonate(1181104-51-7)
• EPA Substance Registry System: methyl hydrogen [(R,S)-1-(benzyloxycarbonylamino)pent-1-yl]phosphonate(1181104-51-7)

Safety Data

• Hazardous Substances Data: 1181104-51-7(Hazardous Substances Data)

Upstream product

• 1181104-50-6 dimethyl [(R,S)-1-(benzyloxycarbonylamino)pentyl]phosphonate 
• 110-62-3 pentanal 
• 621-84-1 O-benzyl carbamate 
• 156336-40-2 diphenyl <1-(1-N-benzyloxycarbonylamino)pentyl>phosphonate 
• 1046116-51-1 methyl ((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)phosphinate 
• 115947-49-4 [1-[(diphenylmethyl)amino]pentyl]phosphinic acid 
• 106019-41-4 [1-[[(phenylmethoxy)carbonyl]amino]pentyl]phosphinic acid 
• 115947-50-7 (1-aminopentyl)phosphinic acid 

Downstream Products

• 1181104-55-1 {[(R,S)-1-benzyloxycarbonylaminopentyl(methoxy)phosphoryl]oxy}acetamide 
• 1181104-56-2 benzyl {[(R,S)-1-benzyloxycarbonylaminopentyl(methoxy)phosphoryl]oxy}acetate 
• 1067680-11-8 [((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(hydroxy)phosphoryl]acetic acid 
• 1261301-07-8 [((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(hydroxy)phosphoryl]acetamide 
• 1261301-09-0 O-methyl S-phenyl ((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)phosphonothiate 
• 1261301-10-3 methyl [((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(methoxy)phosphoryl]acetate 
• 1261301-11-4 [((R,S)-1-{[(benzyloxy)carbonyl]amino}pent-1-yl)(methoxy)phosphoryl]acetamide 

Relevant articles and documents

Synthesis of α-carboxyphosphinopeptides derived from norleucine

In the present study, we describe in detail the synthesis of a relatively rare class of phosphorus compounds, α-carboxyphosphinopeptides. We prepared several norleucine-derived α-carboxyphosphinic pseudopeptides of the general formula Nle-Ψ[PO(OH)]-Gly. These compounds could have important applications as transition state-mimicking inhibitors for methionine or leucine aminopeptidases or other enzymes. For the preparation of the key α-carboxyphosphinate protected precursors, we investigated, compared and improved two different synthetic methods described in literature: the Arbuzov reaction of a silylated N-protected phosphinic acid with a bromoacetate ester and the nucleophilic addition of a mixed O-methyl S-phenyl N-protected phosphonic acid or a methyl N-protected phosphonochloridate with tert-butyl lithioacetate. We also prepared two N-Fmoc protected synthons, Fmoc-Nle-Ψ[PO(OH)]-Gly-COOH and Fmoc-Nle-Ψ[PO(OAd)]-Gly-COOH, and demonstrated that these precursors are suitable building blocks for the solid-phase synthesis of α-carboxyphosphinopeptides.

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.