(S)-N^α-benzyloxycarbonyl-o-bromophenylalanine methyl ester

Base Information

• Chemical Name: (S)-N^α-benzyloxycarbonyl-o-bromophenylalanine methyl ester
• CAS No.: 445417-35-6
• Molecular Formula: C₁₈H₁₈BrNO₄
• Molecular Weight: 392.249
• Mol file: 445417-35-6.mol

Synonyms:(S)-N^α-benzyloxycarbonyl-o-bromophenylalanine methyl ester

Chemical Property of (S)-N^α-benzyloxycarbonyl-o-bromophenylalanine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (S)-N^α-benzyloxycarbonyl-o-bromophenylalanine methyl ester

There total 3 articles about (S)-N^α-benzyloxycarbonyl-o-bromophenylalanine methyl 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: 97.0%

N-benzyloxycarbonyl-β-(2-bromophenyl)-α-dehydroalanine methyl ester (445417-39-0) → (S)-Nα-benzyloxycarbonyl-o-bromophenylalanine methyl ester (445417-35-6)

Guidance literature:

With hydrogen; (+)-1,2-bis((2S,5S)-2,5-diethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; In methanol; for 24h; under 3361.46 Torr;

DOI:10.1016/S0040-4039(02)00249-6

Reference yield:

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) → (S)-Nα-benzyloxycarbonyl-o-bromophenylalanine methyl ester (445417-35-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / DBU / CH₂Cl₂ / 5 h / 20 °C

2: 96 percent / H₂ / (S,S)-(COD)[(Et-DuPHOS)Rh]OTf / methanol / 24 h / 3361.46 Torr

With hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-1,2-bis-((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; In methanol; dichloromethane; 1: Horner-Emmons olefination;

DOI:10.1016/S0040-4020(02)00588-4

Reference yield:

ortho-bromobenzaldehyde (6630-33-7) → (S)-Nα-benzyloxycarbonyl-o-bromophenylalanine methyl ester (445417-35-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / DBU / CH₂Cl₂ / 5 h / 20 °C

2: 96 percent / H₂ / (S,S)-(COD)[(Et-DuPHOS)Rh]OTf / methanol / 24 h / 3361.46 Torr

With hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-1,2-bis-((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; In methanol; dichloromethane; 1: Horner-Emmons olefination;

DOI:10.1016/S0040-4020(02)00588-4

upstream raw materials:

N-benzyloxycarbonyl-β-(2-bromophenyl)-α-dehydroalanine methyl ester

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

ortho-bromobenzaldehyde