89525-23-5

Basic information

• Product Name: 2-Pentenoic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (Z)-
• CAS NO: 89525-23-5
• Molecular Formula: C14H17NO4
• Molecular Weight: 263.293
• Mol File: 89525-23-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Pentenoic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pentenoic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (Z)-(89525-23-5)
• EPA Substance Registry System: 2-Pentenoic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (Z)-(89525-23-5)

Safety Data

• Hazardous Substances Data: 89525-23-5(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 621-84-1 O-benzyl carbamate 
• 1821-02-9 2-oxopentanoic acid 
• 1191124-96-5 N-benzyloxycarbonyl-α-(diphenylphosphono)glycine methyl ester 
• 123-38-6 propionaldehyde 
• 127357-37-3 methyl 2-(benzyloxycarbonylamino)-2-methoxyacetate 
• 127357-38-4 N-(benzyloxycarbonyl)-α-hydroxy-glycine methyl ester 
• 100945-15-1 N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester 

Downstream Products

• 138942-75-3 (R)-(-)-methyl 2-benzyloxycarbonylaminopentanoate 

Relevant articles and documents

The stereoselective construction of E- and Z-Δ-Ile from E-dehydroamino acid ester: the synthesis of the phomopsin A tripeptide side chain

The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy)carbonyl)amino)-2-(diphenoxyphosphoryl)acetate as a common synthetic precursor for the synthesis of E-Δ-dehydroisoleucine and E-Δ-aspartate.

Diastereoselective formation of (Z)-didehydroamino acid esters

The rearrangement of (E)-didehydroamino acid derivatives to the corresponding Z-derivatives under acid or basic catalysis as well as under the influence of radicals has been investigated. The condensation of N-benzyloxycarbonyl or N-tert-butoxycarbonyl protected alkyl 2-amino-2-(dimethoxyphosphoryl)acetates with aldehydes or ketones in dichloromethane in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene furnishes (Z)-didehydroamino acid ester derivatives diastereoselectively in excellent yields and with high purity.

Amino Acids and Peptides; XLIII. Dehydroamino Acids; XVIII. Synthesis of Dehydroamino Acids and Amino Acids from N-Acyl-2-(dialkyloxyphosphinyl)-glycin Esters; II

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