83945-01-1

Basic information

• Product Name: N-benzyloxycarbonyl-(R)alanyl-glycine methyl ester
• Synonyms: N-benzyloxycarbonyl-(R)alanyl-glycine methyl ester
• CAS NO: 83945-01-1
• Molecular Weight: 294.307
• Mol File: 83945-01-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: N-benzyloxycarbonyl-(R)alanyl-glycine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyloxycarbonyl-(R)alanyl-glycine methyl ester(83945-01-1)
• EPA Substance Registry System: N-benzyloxycarbonyl-(R)alanyl-glycine methyl ester(83945-01-1)

Safety Data

• Hazardous Substances Data: 83945-01-1(Hazardous Substances Data)

Upstream product

• 29575-31-3 2-Benzyloxycarbonylamino-propionic acid (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester 
• 616-34-2 methoxycarbonylmethylamine 
• 29575-31-3 2-Benzyloxycarbonylamino-propionic acid (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester 
• 26607-51-2 N-benzyloxycarbonyl-D-alanine 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 4132-86-9 N-benzyloxycarbonylalanine 

Downstream Products

• 145763-51-5 (S)-2-{(S)-2-[2-((R)-2-{2-Benzyloxycarbonylamino-3-[4-(toluene-4-sulfonyloxy)-phenyl]-propionylamino}-propionylamino)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester 
• 145763-41-3 N-benzyloxycarbonyl-O-tosyl-(Z)dehydrotyrosyl-(R)alanyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester 
• 83544-70-1 L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine 2-aminoethylamide 
• 83891-98-9 N-benzyloxycarbonyl-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine 2-aminoethylamide 
• 83892-13-1 N-benzyloxycarbonyl-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine butylamide 
• 83892-12-0 N-benzyloxycarbonyl-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine diethylamide 
• 85148-72-7 N-benzyloxycarbonyl-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine hydrazide 
• 83892-11-9 N-benzyloxycarbonyl-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine dimethylamide 
• 83892-16-4 N-benzyloxycarbonyl-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine methyl ester 
• 83891-97-8 N-benzyloxycarbonyl-L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine N-methylamine 
• 83891-95-6 L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine butylamide 
• 67586-37-2 L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine diethylamide 
• 85148-73-8 L-tyrpsyl-D-alanylglycyl-L-phenylalanyl-L-leucine hydrazide 
• 83891-93-4 L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine N-methylamide 

Relevant articles and documents

1,3-Oxazolidin-5-ones derived from proline as chiral components in the synthesis of predictive enantioselective coupling reagents

1,3-Oxazolidin-5-ones derived from both enantiomers of proline and trichloroacetaldehyde were prepared and applied as an amine component in the synthesis of chiral predictive triazine-based coupling reagents. The reagents were found to be useful in condensations yielding enantiomerically enriched products from racemic substrates.

Intermolecular Aminolyses of 1-Thioglycosyl Esters of N-Acylamino Acids

Fully acetylated 1-thioglycopyranosyl esters of N-acylamino acids (1-3), comprising different 1-thio sugars, undergo aminolysis with glycine methyl ester in dichloromethane at 40° to form the corresponding N-acyldipeptide methyl esters. The relative reactivity of the C-1 thioester bond towards aminolysis depends inter alia on the structure of the sugar moiety. Acylating efficiency of the 1-thioesters was additionally demonstrated by aminolysis of 2,3,4,6-tetra-O-acetyl-1-S-(N-tert-butyloxycarbonyl-L-tyrosyl)-1-thio-β-D- glucopyranose (3h) with peptidoglycan monomer (PGM, a disaccharide-pentapeptide) in N,N-dimethylformamide at room temperature to give the corresponding disaccharide-hexapeptide.

PEPTIDE BOND FORMATION BY INTERMOLECULAR AMINOLYSIS OF D-GLUCOPYRANOSYL ESTERS OF AMINO ACIDS

The reaction of HO-protected and -unprotected D-glucopyranosyl esters of N-acylamino acids (Gly, Ala, Phe) with glycine and phenylalanine methyl esters in N,N-dimethylformamide at 38 deg C and dichloromethane at 40 deg C, respectively, led to repture of the C-1 ester bond and formation of the corresponding N-acyldipeptide methyl ester.The relative reactivity of the C-1 ester bond toward aminolysis was greatly influenced by the structure of the amino acid nucleophile, the nature of the aglycon side-chain group, and the anomeric configuration of the D-glucopyranosyl ester involved.Evidence for a substantially lower acylating efficiency of the ester at C-2, as compared to that at C-1, was obtained by aminolysis of two fully acetylated 2-O-(acylaminoacyl)-β-D-glucopyranoses.Treatment of 1-O-(glycylglycylglycyl)-β-D-glucopyranose with phenylalanine methyl ester in N,N-dimethylformamide led to parallel hydrolysis and intermolecular aminolysis, to give the tripeptide and tetrapeptide methyl ester.