L-N^α-benzyloxycarbonyl-4-[1-(2-ethenyl)]phenylalanine benzyl ester

Base Information

• Chemical Name: L-N^α-benzyloxycarbonyl-4-[1-(2-ethenyl)]phenylalanine benzyl ester
• CAS No.: 257628-01-6
• Molecular Formula: C₂₆H₂₅NO₄
• Molecular Weight: 415.489
• Mol file: 257628-01-6.mol

Synonyms:L-N^α-benzyloxycarbonyl-4-[1-(2-ethenyl)]phenylalanine benzyl ester

Chemical Property of L-N^α-benzyloxycarbonyl-4-[1-(2-ethenyl)]phenylalanine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-N^α-benzyloxycarbonyl-4-[1-(2-ethenyl)]phenylalanine benzyl ester

There total 1 articles about L-N^α-benzyloxycarbonyl-4-[1-(2-ethenyl)]phenylalanine benzyl ester 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: 73.0%

tri-n-butyl(vinyl)tin (7486-35-3) + L-Nα-Cbz-4-(O-trifluoromethanesulfonate)tyrosine benzyl ester (183070-41-9) → L-Nα-benzyloxycarbonyl-4-[1-(2-ethenyl)]phenylalanine benzyl ester (257628-01-6)

Guidance literature:

With PdCl₂(PPh)3; lithium chloride; In N,N-dimethyl-formamide; at 90 ℃; for 24h;

DOI:10.1016/S0957-4166(99)00385-7

Reference yield: 85.0%

L-Nα-benzyloxycarbonyl-4-[1-(2-ethenyl)]phenylalanine benzyl ester (257628-01-6) → L-Nα-benzyloxycarbonyl-4-(1,2-dihydroxyethyl)phenylalanine benzyl ester (257628-02-7)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tert-butyl alcohol; at 20 ℃;

DOI:10.1016/S0957-4166(99)00385-7

Reference yield:

L-Nα-benzyloxycarbonyl-4-[1-(2-ethenyl)]phenylalanine benzyl ester (257628-01-6) → L-4-((di-tert-butyl)phosphonomethyl)phenylalanine (257628-04-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 85 percent / 4-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol / 20 °C

2.1: 94 percent / aq. NaIO₄ / diethyl ether / 3 h / 20 °C

3.1: 99 percent / NaBH₄; EtOH / tetrahydrofuran / 0.33 h / 0 °C

4.1: 79 percent / CBr₄; Ph₃P / acetonitrile / 0.5 h / 20 °C

5.1: LHMDS; HMPA / tetrahydrofuran / 0.5 h / -78 °C

5.2: 57 percent / tetrahydrofuran / 4 h / -78 - 0 °C

6.1: 99 percent / H₂ / Pd / methanol / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; ethanol; carbon tetrabromide; hydrogen; 4-methylmorpholine N-oxide; triphenylphosphine; lithium hexamethyldisilazane; palladium; In tetrahydrofuran; methanol; diethyl ether; acetonitrile; tert-butyl alcohol; 1.1: Oxidation / 2.1: oxidative cleavage / 3.1: Reduction / 4.1: Substitution / 5.1: Metallation / 5.2: Substitution / 6.1: Hydrogenolysis;

DOI:10.1016/S0957-4166(99)00385-7

upstream raw materials:

tri-n-butyl(vinyl)tin

L-N^α-Cbz-4-(O-trifluoromethanesulfonate)tyrosine benzyl ester

Downstream raw materials:

L-N^α-benzyloxycarbonyl-4-(1,2-dihydroxyethyl)phenylalanine benzyl ester

L-4-((di-tert-butyl)phosphonomethyl)phenylalanine

L-N^α-benzyloxycarbonyl-4-(formyl)phenylalanine benzyl ester

L-N^α-benzyloxycarbonyl-4-(bromomethyl)phenylalanine benzyl ester