(S)-2-Benzyloxycarbonylamino-3-[(S)-3-(4-methoxy-phenyl)-2-methylamino-propionyloxy]-butyric acid allyl ester; compound with trifluoro-acetic acid

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-3-[(S)-3-(4-methoxy-phenyl)-2-methylamino-propionyloxy]-butyric acid allyl ester; compound with trifluoro-acetic acid
• CAS No.: 117710-23-3
• Molecular Formula: C₂HF₃O₂*C₂₆H₃₂N₂O₇
• Molecular Weight: 598.573
• Mol file: 117710-23-3.mol

Synonyms:(S)-2-Benzyloxycarbonylamino-3-[(S)-3-(4-methoxy-phenyl)-2-methylamino-propionyloxy]-butyric acid allyl ester; compound with trifluoro-acetic acid

Chemical Property of (S)-2-Benzyloxycarbonylamino-3-[(S)-3-(4-methoxy-phenyl)-2-methylamino-propionyloxy]-butyric acid allyl ester; compound with trifluoro-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzyloxycarbonylamino-3-[(S)-3-(4-methoxy-phenyl)-2-methylamino-propionyloxy]-butyric acid allyl ester; compound with trifluoro-acetic acid

There total 5 articles about (S)-2-Benzyloxycarbonylamino-3-[(S)-3-(4-methoxy-phenyl)-2-methylamino-propionyloxy]-butyric acid allyl ester; compound with trifluoro-acetic acid 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: 90.0%

allyl N-(benzyloxycarbonyl)-O--L-threoninate (117710-13-1) + trifluoroacetic acid (76-05-1) → (S)-2-Benzyloxycarbonylamino-3-[(S)-3-(4-methoxy-phenyl)-2-methylamino-propionyloxy]-butyric acid allyl ester; compound with trifluoro-acetic acid (117710-23-3)

Guidance literature:

for 0.5h;

DOI:10.1021/jo00264a022

Reference yield:

N-[(phenylmethoxy)carbonyl]-L-threonine (19728-63-3) → (S)-2-Benzyloxycarbonylamino-3-[(S)-3-(4-methoxy-phenyl)-2-methylamino-propionyloxy]-butyric acid allyl ester; compound with trifluoro-acetic acid (117710-23-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / Cs₂CO₃ / dimethylformamide / 2 h

2: 98 percent / triethylamine (TEA), 4-(dimethylamino)pyridine (DMAP), isopropenyl chlorocarbonate (IPCC) / CH₂Cl₂ / 0.5 h / -5 °C

3: 90 percent / 0.5 h

With dmap; Isopropenyl chloroformate; caesium carbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00264a022

Reference yield:

methyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-N,O-dimethyl-L-tyrosinate (117710-21-1) → (S)-2-Benzyloxycarbonylamino-3-[(S)-3-(4-methoxy-phenyl)-2-methylamino-propionyloxy]-butyric acid allyl ester; compound with trifluoro-acetic acid (117710-23-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / 2 N NaOH / methanol / 0 - 5 °C

2: 98 percent / triethylamine (TEA), 4-(dimethylamino)pyridine (DMAP), isopropenyl chlorocarbonate (IPCC) / CH₂Cl₂ / 0.5 h / -5 °C

3: 90 percent / 0.5 h

With dmap; sodium hydroxide; Isopropenyl chloroformate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo00264a022

upstream raw materials:

allyl N-(benzyloxycarbonyl)-O--L-threoninate

trifluoroacetic acid

N-[(phenylmethoxy)carbonyl]-L-threonine

methyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-N,O-dimethyl-L-tyrosinate

Downstream raw materials:

allyl N-(benzyloxycarbonyl)-O-<-(N,O-dimethyl-L-tyrosyl)>-L-threoninate