[(E)-(S)-4-Hydroxy-1-(4-methoxy-phenyl)-but-2-enyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(E)-(S)-4-Hydroxy-1-(4-methoxy-phenyl)-but-2-enyl]-carbamic acid tert-butyl ester
• CAS No.: 156325-00-7
• Molecular Formula: C₁₆H₂₃NO₄
• Molecular Weight: 293.363
• Mol file: 156325-00-7.mol

Synonyms:[(E)-(S)-4-Hydroxy-1-(4-methoxy-phenyl)-but-2-enyl]-carbamic acid tert-butyl ester

Chemical Property of [(E)-(S)-4-Hydroxy-1-(4-methoxy-phenyl)-but-2-enyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(E)-(S)-4-Hydroxy-1-(4-methoxy-phenyl)-but-2-enyl]-carbamic acid tert-butyl ester

There total 5 articles about [(E)-(S)-4-Hydroxy-1-(4-methoxy-phenyl)-but-2-enyl]-carbamic acid tert-butyl 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: 92.0%

(E)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid ethyl ester (156324-99-1) → [(E)-(S)-4-Hydroxy-1-(4-methoxy-phenyl)-but-2-enyl]-carbamic acid tert-butyl ester (156325-00-7)

Guidance literature:

With boron trifluoride diethyl etherate; diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)75803-5

Reference yield:

N-(tert-butoxycarbonyl)-D-(4-hydroxyphenyl)glycine (27460-85-1) → [(E)-(S)-4-Hydroxy-1-(4-methoxy-phenyl)-but-2-enyl]-carbamic acid tert-butyl ester (156325-00-7)

Guidance literature:

Multi-step reaction with 5 steps

1: (C₂H₅O)2P(O)CN, Et₃N / dimethylformamide / 18 h / 4 °C

2: K₂CO₃ / dimethylformamide / 7 h / Ambient temperature

3: 1M LAH / diethyl ether / 0.5 h / -15 - -7 °C

4: CH₂Cl₂ / 1 h / 0 °C

5: 92 percent / 1M DIBAL, BF₃*OEt₂ / hexane; CH₂Cl₂ / 0.5 h / -78 °C

With lithium aluminium tetrahydride; diethyl cyanophosphonate; boron trifluoride diethyl etherate; diisobutylaluminium hydride; potassium carbonate; triethylamine; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)75803-5

Reference yield:

(R)-(1-(4-methoxyphenyl)-2-oxoethyl) tert-butyl carbamate (850166-76-6) → [(E)-(S)-4-Hydroxy-1-(4-methoxy-phenyl)-but-2-enyl]-carbamic acid tert-butyl ester (156325-00-7)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 1 h / 0 °C

2: 92 percent / 1M DIBAL, BF₃*OEt₂ / hexane; CH₂Cl₂ / 0.5 h / -78 °C

With boron trifluoride diethyl etherate; diisobutylaluminium hydride; In hexane; dichloromethane;

DOI:10.1016/S0040-4039(00)75803-5

upstream raw materials:

(E)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid ethyl ester

N-(tert-butoxycarbonyl)-D-(4-hydroxyphenyl)glycine

(R)-(1-(4-methoxyphenyl)-2-oxoethyl) tert-butyl carbamate

[(R)-(4-Hydroxy-phenyl)-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester

Downstream raw materials:

Acetic acid (1S,2S)-2,3-diacetoxy-1-[(R)-tert-butoxycarbonylamino-(4-methoxy-phenyl)-methyl]-propyl ester

Acetic acid (1R,2R)-2,3-diacetoxy-1-[(R)-tert-butoxycarbonylamino-(4-methoxy-phenyl)-methyl]-propyl ester