1181104-62-0

Basic information

• Product Name: methyl (2S)-2-[({[(R,S)-1-benzyloxycarbonylaminopentyl(benzyloxy)phosphoryl]oxy}acetyl)amino]-3-methylbutanoate
• Synonyms: methyl (2S)-2-[({[(R,S)-1-benzyloxycarbonylaminopentyl(benzyloxy)phosphoryl]oxy}acetyl)amino]-3-methylbutanoate
• CAS NO: 1181104-62-0
• Molecular Weight: 562.6
• Mol File: 1181104-62-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl (2S)-2-[({[(R,S)-1-benzyloxycarbonylaminopentyl(benzyloxy)phosphoryl]oxy}acetyl)amino]-3-methylbutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2S)-2-[({[(R,S)-1-benzyloxycarbonylaminopentyl(benzyloxy)phosphoryl]oxy}acetyl)amino]-3-methylbutanoate(1181104-62-0)
• EPA Substance Registry System: methyl (2S)-2-[({[(R,S)-1-benzyloxycarbonylaminopentyl(benzyloxy)phosphoryl]oxy}acetyl)amino]-3-methylbutanoate(1181104-62-0)

Safety Data

• Hazardous Substances Data: 1181104-62-0(Hazardous Substances Data)

Upstream product

• 621-84-1 O-benzyl carbamate 
• 538-60-3 dibenzyl hydrogen phosphite 
• 6306-52-1 L-valine methylester hydrochloride 
• 501-53-1 benzyl chloroformate 
• 13138-37-9 1-amino-pentylphosphonic acid 
• 110-62-3 pentanal 
• 80088-88-6 [(R,S)-1-(benzyloxycarbonylamino)pentyl]phosphonic acid 
• 1043504-42-2 dibenzyl [(R,S)-1-(benzyloxycarbonylamino)pentyl]phosphonate 
• 106019-45-8 benzyl hydrogen [(R,S)-1-(benzyloxycarbonylamino)pent-1-yl]phosphonate 

Relevant articles and documents

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.