142056-02-8

Basic information

• Product Name: 2-Butenedioic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, 4-(1,1-dimethylethyl) 1-methyl ester, (Z)-
• CAS NO: 142056-02-8
• Molecular Formula: C17H21NO6
• Molecular Weight: 335.357
• Mol File: 142056-02-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-Butenedioic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, 4-(1,1-dimethylethyl) 1-methyl ester, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butenedioic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, 4-(1,1-dimethylethyl) 1-methyl ester, (Z)-(142056-02-8)
• EPA Substance Registry System: 2-Butenedioic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, 4-(1,1-dimethylethyl) 1-methyl ester, (Z)-(142056-02-8)

Safety Data

• Hazardous Substances Data: 142056-02-8(Hazardous Substances Data)

Upstream product

• 7633-32-1 tert-butyl glyoxylate 
• 100945-15-1 N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester 

Downstream Products

• 142056-11-9 (S)-4-((Z)-2-Benzyloxycarbonylamino-3-tert-butoxycarbonyl-acryloylamino)-4-((S)-1-methoxycarbonyl-ethylcarbamoyl)-butyric acid benzyl ester 
• 142056-10-8 (Z)-3-Benzyloxycarbonylamino-3-((S)-1-methoxycarbonyl-ethylcarbamoyl)-acrylic acid tert-butyl ester 
• 142056-04-0 (Z)-2-Benzyloxycarbonylamino-but-2-enedioic acid 4-tert-butyl ester 

Relevant articles and documents

Reactivity of dehydroaspartic acid derivatives under peptide coupling conditions

The reactivity of α-carboxy-activated dehydroaspartic acid derivatives with various N- and O-nucleophiles is described for the first time. Reaction of amino acid derivatives with Ac-Δ(Z)Asp(OBu(t))-OH (4a) under a variety of coupling conditions gave very poor yields of the resulting dehydroaspartyl dipeptides, while the coupling of 4a with oxygen nucleophiles gave very good yields of the dehydroaspartyl esters. In contrast, the coupling of amino acids with Cbz-Δ(Z)Asp(Obu(t))-OH (4b) gave good yields of dehydroaspartyl dipeptides. The formation of a highly reactive oxazolone intermediate is proposed to explain the low yields of peptide coupling between 4a and amino acids.