(S)-2-Benzyloxycarbonylamino-3-[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-3-[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester
• CAS No.: 600737-81-3
• Molecular Formula: C₃₁H₃₆BNO₇
• Molecular Weight: 545.44
• Mol file: 600737-81-3.mol

Synonyms:(S)-2-Benzyloxycarbonylamino-3-[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester

Chemical Property of (S)-2-Benzyloxycarbonylamino-3-[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzyloxycarbonylamino-3-[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester

There total 5 articles about (S)-2-Benzyloxycarbonylamino-3-[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid 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: 82.0%

bis(pinacol)diborane (73183-34-3) + (S)-2-Benzyloxycarbonylamino-3-(3-iodo-4-methoxy-phenyl)-propionic acid benzyl ester (600737-78-8) → (S)-2-Benzyloxycarbonylamino-3-[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester (600737-81-3)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 80 ℃; for 24h;

DOI:10.1016/S0040-4039(03)01081-5

Reference yield:

(S)-2-Benzyloxycarbonylamino-3-(4-hydroxy-3-iodo-phenyl)-propionic acid benzyl ester (213757-66-5) → (S)-2-Benzyloxycarbonylamino-3-[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester (600737-81-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / potassium carbonate / dimethylformamide / 72 h / 20 °C

2: 82 percent / Pd(dppf)Cl₂*CH₂Cl₂; KOAc / dimethylsulfoxide / 24 h / 80 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; potassium carbonate; In dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo051076m

Reference yield:

benzyl N-carbobenzyloxy-L-tyrosine (5513-40-6) → (S)-2-Benzyloxycarbonylamino-3-[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester (600737-81-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 43 percent / silver sulfate; iodine / methanol / 5 h / 20 °C

2: 68 percent / potassium carbonate / dimethylformamide / 72 h / 20 °C

3: 82 percent / Pd(dppf)Cl₂*CH₂Cl₂; KOAc / dimethylsulfoxide / 24 h / 80 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; iodine; potassium acetate; potassium carbonate; silver sulfate; In methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo051076m

upstream raw materials:

bis(pinacol)diborane

(S)-2-Benzyloxycarbonylamino-3-(3-iodo-4-methoxy-phenyl)-propionic acid benzyl ester

benzyl N-carbobenzyloxy-L-tyrosine

(S)-2-Benzyloxycarbonylamino-3-(4-hydroxy-3-iodo-phenyl)-propionic acid benzyl ester