methyl (S)-2-(benzyloxycarbonylamino)-3-(3-formyl-4-hydroxyphenyl)propionate

Base Information

• Chemical Name: methyl (S)-2-(benzyloxycarbonylamino)-3-(3-formyl-4-hydroxyphenyl)propionate
• CAS No.: 367967-64-4
• Molecular Formula: C₁₉H₁₉NO₆
• Molecular Weight: 357.363
• Mol file: 367967-64-4.mol

Synonyms:methyl (S)-2-(benzyloxycarbonylamino)-3-(3-formyl-4-hydroxyphenyl)propionate

Chemical Property of methyl (S)-2-(benzyloxycarbonylamino)-3-(3-formyl-4-hydroxyphenyl)propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (S)-2-(benzyloxycarbonylamino)-3-(3-formyl-4-hydroxyphenyl)propionate

There total 5 articles about methyl (S)-2-(benzyloxycarbonylamino)-3-(3-formyl-4-hydroxyphenyl)propionate 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: 82.0%

carbon monoxide (201230-82-2) + (S)-N-benzyloxycarbonyl-3-(4-hydroxy-3-iodophenyl)alanine methyl ester (79677-60-4) → methyl (S)-2-(benzyloxycarbonylamino)-3-(3-formyl-4-hydroxyphenyl)propionate (367967-64-4)

Guidance literature:

With triethylsilane; 1,1'-bis-(diphenylphosphino)ferrocene; triethylamine; palladium diacetate; In N,N-dimethyl-formamide; at 80 ℃; for 3h;

DOI:10.1081/scc-100104476

Reference yield: 43.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + N-(benzyloxycarbonyl)-L-tyrosine methyl ester (13512-31-7) → methyl (S)-2-(benzyloxycarbonylamino)-3-(3-formyl-4-hydroxyphenyl)propionate (367967-64-4)

Guidance literature:

With triethylamine; magnesium chloride; In acetonitrile; for 18h; Reflux;

DOI:10.1016/j.bmcl.2009.04.081

Reference yield:

3-Iodo-L-tyrosine (70-78-0) → methyl (S)-2-(benzyloxycarbonylamino)-3-(3-formyl-4-hydroxyphenyl)propionate (367967-64-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / HCl / 2 h / 0 °C

2: 89 percent / Na₂CO₃ / H₂O; diethyl ether / 3 h / 20 °C

3: 82 percent / dppf; Et₃N; Et₃SiH / Pd(OAc)2 / dimethylformamide / 3 h / 80 °C

With hydrogenchloride; triethylsilane; 1,1'-bis-(diphenylphosphino)ferrocene; sodium carbonate; triethylamine; palladium diacetate; In diethyl ether; water; N,N-dimethyl-formamide;

DOI:10.1081/scc-100104476

upstream raw materials:

carbon monoxide

(S)-N-benzyloxycarbonyl-3-(4-hydroxy-3-iodophenyl)alanine methyl ester

3-Iodo-L-tyrosine

benzyl chloroformate

Downstream raw materials:

methyl (S)-2-(benzyloxycarbonylamino)-3-[4-(diethoxyphosphoryloxy)-3-formylphenyl]propionate

N-[(phenylmethoxy)carbonyl]-3-hydroxy-O-(phenylmethyl)-L-tyrosine methyl ester

N-[(phenylmethoxy)carbonyl]-3-formyl-O-(phenylmethyl)-L-tyrosine methyl ester