(S)-3-(5-Acetoxymethyl-2'-chloro-6-trifluoromethanesulfonyloxy-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester

Base Information

• Chemical Name: (S)-3-(5-Acetoxymethyl-2'-chloro-6-trifluoromethanesulfonyloxy-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester
• CAS No.: 206445-95-6
• Molecular Formula: C₂₈H₂₅ClF₃NO₉S
• Molecular Weight: 644.022
• Mol file: 206445-95-6.mol

Synonyms:

Chemical Property of (S)-3-(5-Acetoxymethyl-2'-chloro-6-trifluoromethanesulfonyloxy-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(5-Acetoxymethyl-2'-chloro-6-trifluoromethanesulfonyloxy-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester

There total 6 articles about (S)-3-(5-Acetoxymethyl-2'-chloro-6-trifluoromethanesulfonyloxy-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid 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:

Z-L-Tyr-OH (1164-16-5) → (S)-3-(5-Acetoxymethyl-2'-chloro-6-trifluoromethanesulfonyloxy-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester (206445-95-6)

Guidance literature:

Multi-step reaction with 7 steps

1: Na₂B₄O₇*10H₂, 1M NaOH / 120 h / 40 °C

2: Br₂, NaOAc / acetic acid / 0.5 h / 15 °C

3: TsOH / 3 h / Heating

4: 89 percent / TsOH / tetrahydrofuran / 4.5 h / 55 °C / Heating

5: Na₂CO₃, Pd(OAc)2, PPh₃ / ethanol; toluene / 2 h / Heating; ultrasonication

6: TsOH / 3 h / 70 °C

7: (iPr)2EtN / CH₂Cl₂ / 1 h / -65 °C

With palladium diacetate; borax; sodium hydroxide; bromine; sodium acetate; sodium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; acetic acid; toluene;

DOI:10.1002/hlca.19980810322

Reference yield:

(S)-N-benzyloxycarbonyl-4-hydroxy-3-hydroxymethylphenylalanine (52186-44-4) → (S)-3-(5-Acetoxymethyl-2'-chloro-6-trifluoromethanesulfonyloxy-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester (206445-95-6)

Guidance literature:

Multi-step reaction with 6 steps

1: Br₂, NaOAc / acetic acid / 0.5 h / 15 °C

2: TsOH / 3 h / Heating

3: 89 percent / TsOH / tetrahydrofuran / 4.5 h / 55 °C / Heating

4: Na₂CO₃, Pd(OAc)2, PPh₃ / ethanol; toluene / 2 h / Heating; ultrasonication

5: TsOH / 3 h / 70 °C

6: (iPr)2EtN / CH₂Cl₂ / 1 h / -65 °C

With palladium diacetate; bromine; sodium acetate; sodium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; acetic acid; toluene;

DOI:10.1002/hlca.19980810322

Reference yield:

(S)-2-Benzyloxycarbonylamino-3-(3-bromo-4-hydroxy-5-hydroxymethyl-phenyl)-propionic acid → (S)-3-(5-Acetoxymethyl-2'-chloro-6-trifluoromethanesulfonyloxy-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester (206445-95-6)

Guidance literature:

Multi-step reaction with 5 steps

1: TsOH / 3 h / Heating

2: 89 percent / TsOH / tetrahydrofuran / 4.5 h / 55 °C / Heating

3: Na₂CO₃, Pd(OAc)2, PPh₃ / ethanol; toluene / 2 h / Heating; ultrasonication

4: TsOH / 3 h / 70 °C

5: (iPr)2EtN / CH₂Cl₂ / 1 h / -65 °C

With palladium diacetate; sodium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1002/hlca.19980810322

upstream raw materials:

Z-L-Tyr-OH

(S)-N-benzyloxycarbonyl-4-hydroxy-3-hydroxymethylphenylalanine

N-(benzyloxycarbonyl)-3-bromo-5-(hydroxymethyl)-(S)-tyrosine methyl ester

(S)-2-Benzyloxycarbonylamino-3-(8-bromo-2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)-propionic acid methyl ester

Downstream raw materials:

(S)-3-(5-Acetoxymethyl-2'-chloro-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester

(S)-2-Benzyloxycarbonylamino-3-(5-bromomethyl-2'-chloro-biphenyl-3-yl)-propionic acid methyl ester