83317-18-4

Basic information

• Product Name: 2-Pentenoic acid, 4-methyl-2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (Z)-
• CAS NO: 83317-18-4
• Molecular Formula: C15H19NO4
• Molecular Weight: 277.32
• Mol File: 83317-18-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Pentenoic acid, 4-methyl-2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pentenoic acid, 4-methyl-2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (Z)-(83317-18-4)
• EPA Substance Registry System: 2-Pentenoic acid, 4-methyl-2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (Z)-(83317-18-4)

Safety Data

• Hazardous Substances Data: 83317-18-4(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 816-66-0 4-methyl-2-oxopentanoic acid 
• 621-84-1 O-benzyl carbamate 
• 1191124-96-5 N-benzyloxycarbonyl-α-(diphenylphosphono)glycine methyl ester 
• 78-84-2 isobutyraldehyde 
• 100945-15-1 N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester 
• 114684-69-4 methyl 2-(benzyloxycarbonylamino)-2-(diethyloxyphosphoryl)acetate 

Downstream Products

• 154700-98-8 ((Z)-1-Formyl-3-methyl-but-1-enyl)-carbamic acid benzyl ester 
• 154700-91-1 ((Z)-1-Hydroxymethyl-3-methyl-but-1-enyl)-carbamic acid benzyl ester 

Relevant articles and documents

Stereoselective Synthesis of (E)-α,β-dehydroamino acid esters

Dehydroamino acid (Dhaa) is recognized as a useful tool or substrate for amino acid and peptide research. Although the stereoselective synthesis of the thermodynamically more stable Z-Dhaa has been well examined and established, the stereoselective synthesis of E-Dhaa has still remained to be a challenging synthetic task. In this paper, a stereoselective synthesis of E-Dhaa esters using a new (α-diphenylphosphono)glycine is described. The characteristic aspects of the new method are summarized as follows: (i) metal additives play an important role in the promotion of E-stereoselectivities. (ii) the use of NaI was effected for the synthesis of E-Dhaas bearing an aryl substituent and an amino functionality, (iii) MgBr2·OEt2 and ZnCl 2 contributed to improve the E-stereoselective synthesis of E-Dhaas bearing an alkyl substituent and an oxygen functionality, (iv) various protecting and functional groups were compatible under the reaction conditions, and (v) N-Cbz, Boc, and acyl-α-(diphenylphosphono)glycines were served for the stereoselective olefination reaction to provide the corresponding E-Dhaas. A variety of (E)-dehydroamino acid esters were stereoselectively synthesized by using (diphenylphosphono)glycinate. The stereoselectivity was influenced by metal additives. Various (E)-dehydroamino acid esters were prepared by the condensation reaction of the new phosphonates with easily available aldehydes by choosing the appropriate reaction conditions.

Deconjugation of dehydroamino acids: Stereoselective synthesis of racemic (E)-vinylglycines

(Chemical Equation Presented) A practical and general two-step synthesis of carbamate-protected (E)-vinylglycines from aliphatic aldehydes is reported. The key step involves the kinetic α-protonation of dianionic dienolates derived from dehydroamino acids

Dehydrooligopeptides. XII. Convenient synthesis of various kinds of N-benzyloxycarbonyl-α-dehydroamino acid methyl esters

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