(S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-methyl-pentanoic acid allyl ester

Base Information

• Chemical Name: (S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-methyl-pentanoic acid allyl ester
• CAS No.: 222737-12-4
• Molecular Formula: C₃₄H₄₁N₂O₈P
• Molecular Weight: 636.682
• Mol file: 222737-12-4.mol

Synonyms:(S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-methyl-pentanoic acid allyl ester

Chemical Property of (S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-methyl-pentanoic acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-methyl-pentanoic acid allyl ester

There total 4 articles about (S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-methyl-pentanoic acid allyl 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:

N-acetyl-L-tyrosine (537-55-3) → (S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-methyl-pentanoic acid allyl ester (222737-12-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) tert-butyldimethylsilyl chloride, N-methylmorpholine, 2.) 1H-tetrazole / 1.) THF, 5 min, 2.) THF, 3 h

2: aq. tert-butylhydroperoxide / 1.5 h / 0 - 20 °C

3: 1.) 1,3-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole, 2.) N-methylmorpholine / 1.) THF, RT, 30 min, 2.) THF, RT, 4 h

With 4-methyl-morpholine; 1H-tetrazole; tert.-butylhydroperoxide; benzotriazol-1-ol; tert-butyldimethylsilyl chloride; dicyclohexyl-carbodiimide;

DOI:10.1021/jm980612i

Reference yield:

Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) → (S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-methyl-pentanoic acid allyl ester (222737-12-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) tert-butyldimethylsilyl chloride, N-methylmorpholine, 2.) 1H-tetrazole / 1.) THF, 5 min, 2.) THF, 3 h

2: aq. tert-butylhydroperoxide / 1.5 h / 0 - 20 °C

3: 1.) 1,3-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole, 2.) N-methylmorpholine / 1.) THF, RT, 30 min, 2.) THF, RT, 4 h

With 4-methyl-morpholine; 1H-tetrazole; tert.-butylhydroperoxide; benzotriazol-1-ol; tert-butyldimethylsilyl chloride; dicyclohexyl-carbodiimide;

DOI:10.1021/jm980612i

Reference yield:

(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphanyloxy)-phenyl]-propionic acid → (S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-methyl-pentanoic acid allyl ester (222737-12-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. tert-butylhydroperoxide / 1.5 h / 0 - 20 °C

2: 1.) 1,3-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole, 2.) N-methylmorpholine / 1.) THF, RT, 30 min, 2.) THF, RT, 4 h

With 4-methyl-morpholine; tert.-butylhydroperoxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide;

DOI:10.1021/jm980612i

upstream raw materials:

N-acetyl-O-[bis(benzyloxy)phosphoryl]-L-tyrosine

N-acetyl-L-tyrosine

Dibenzyl N,N-diisopropylphosphoramidite