208448-13-9

Basic information

• Product Name: methyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate
• Synonyms: methyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate
• CAS NO: 208448-13-9
• Molecular Weight: 494.501
• Mol File: 208448-13-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate(208448-13-9)
• EPA Substance Registry System: methyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate(208448-13-9)

Safety Data

• Hazardous Substances Data: 208448-13-9(Hazardous Substances Data)

Upstream product

• 208448-12-8 methyl (2R)-2-azido-2-[3,5-bis(benzyloxy)-4-methoxyphenyl]ethanoate 
• 191542-07-1 (2R)-2-azido-2-[3,5-bis(benzyloxy)-4-methoxyphenyl]ethanoic acid 
• 5491-18-9 (S)-N-(benzyloxycarbonyl)phenylglycine 

Relevant articles and documents

Synthesis of a model bicyclic CDE ring system of ristocetin A and observation of a facile inversion of configuration in a 16-membered DE ring model

Areneruthenium chemistry was used to effect intramolecular S(N)Ar reactions between phenoxide nucleophiles and chlorophenylalanine residues that are connected by a peptide chain, resulting in the construction of a bicyclic peptido aryl ether system that corresponds to the BCDF system of the glycopeptide antibiotics ristocetin A and teicoplanin. A facile and selective base-catalyzed complete inversion of configuration at the D ring arylglycine residue was observed when this unit is the carboxylate terminus on a 16- membered ring system corresponding to the DEF rings of the target molecules. The inversion appears to result from an overwhelming thermodynamic preference for the inverted system and is supported by molecular mechanics and semiempirical calculations on the minimized conformations of the epimeric molecules.