N-carboxy-α-dehydrophenylalanine anhydride

Base Information

• Chemical Name: N-carboxy-α-dehydrophenylalanine anhydride
• CAS No.: 74805-42-8
• Molecular Formula: C₁₀H₇NO₃
• Molecular Weight: 189.17
• Mol file: 74805-42-8.mol

Synonyms:N-carboxy-α-dehydrophenylalanine anhydride

Chemical Property of N-carboxy-α-dehydrophenylalanine anhydride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-carboxy-α-dehydrophenylalanine anhydride

There total 7 articles about N-carboxy-α-dehydrophenylalanine anhydride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

(Z)-2-benzyloxycarbonylaminocinnamic acid (72015-61-3) → N-carboxy-α-dehydrophenylalanine anhydride (74805-42-8)

Guidance literature:

With thionyl chloride; In various solvent(s); for 2h; Ambient temperature;

DOI:10.1246/cl.1981.1635

Reference yield: 83.0%

(Z)-2-benzyloxy-4-benzylideneoxazol-5-one (74805-39-3) → N-carboxy-α-dehydrophenylalanine anhydride (74805-42-8)

Guidance literature:

With hydrogenchloride; In chloroform; at 0 ℃; for 0.25h;

Reference yield: 55.0%

phosgene (75-44-5) + 2-azido-3-phenyl-propionic acid (116847-33-7) → N-carboxy-α-dehydrophenylalanine anhydride (74805-42-8)

Guidance literature:

sodium perrhenate; In 1,2-dimethoxyethane; at 85 ℃; for 2.5h;

DOI:10.1055/s-1988-27516

upstream raw materials:

phosgene

2-azido-3-phenyl-propionic acid

(Z)-2-benzyloxycarbonylaminocinnamic acid

(Z)-2-benzyloxy-4-benzylideneoxazol-5-one

Downstream raw materials:

^tBOC-Gly-ΔPhe-(S)-Leu-OMe

^tBOC-Gly-ΔPhe-(S)-Met-OMe

Boc-L-Ala-(Z)-ΔPhe*NCA

(Z)-2-Amino-3-phenyl-acrylic acid isopropyl ester

Refernces

• 1、 Jacquier, Robert,Verducci, Jean. "NOUVELLE SYNTHESE DE LA TENTOXINE". . p. 2775 - 2778. Retrieved 1984.
• 2、 Shin, Chung-gi,Yonezawa, Yasuchika,Yoshimura, Juji. "THE SYNTHESES OF N-FREE α-DEHYDROAMINO ACID ESTERS AND N-ACETYL DEHYDRODIPEPTIDE ESTER FROM N-CARBOXY α-DEHYDROAMINO ACID ANHYDRIDE". . p. 1635 - 1638. Retrieved 2007/10/02.