(Z)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid methyl ester

Base Information

• Chemical Name: (Z)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid methyl ester
• CAS No.: 156325-02-9
• Molecular Formula: C₁₇H₂₃NO₅
• Molecular Weight: 321.373
• Mol file: 156325-02-9.mol

Synonyms:(Z)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid methyl ester

Chemical Property of (Z)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid methyl ester

There total 4 articles about (Z)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic 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: 82.0%

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7) + (R)-(1-(4-methoxyphenyl)-2-oxoethyl) tert-butyl carbamate (850166-76-6) → (Z)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid methyl ester (156325-02-9)

Guidance literature:

With potassium hexamethylsilazane; 18-crown-6 ether; In tetrahydrofuran; toluene; 0 deg C, 30 min -> -78 deg C, 4 h;

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

Reference yield:

N-(tert-butoxycarbonyl)-D-(4-hydroxyphenyl)glycine (27460-85-1) → (Z)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid methyl ester (156325-02-9)

Guidance literature:

Multi-step reaction with 4 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: 82 percent / 0.5M KN(TMS)2 / 18-crown-6 / toluene; tetrahydrofuran / 0 deg C, 30 min -> -78 deg C, 4 h

With lithium aluminium tetrahydride; diethyl cyanophosphonate; potassium hexamethylsilazane; potassium carbonate; triethylamine; 18-crown-6 ether; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; toluene;

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

Reference yield:

[(R)-(4-Hydroxy-phenyl)-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester (156324-97-9) → (Z)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid methyl ester (156325-02-9)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / dimethylformamide / 7 h / Ambient temperature

2: 1M LAH / diethyl ether / 0.5 h / -15 - -7 °C

3: 82 percent / 0.5M KN(TMS)2 / 18-crown-6 / toluene; tetrahydrofuran / 0 deg C, 30 min -> -78 deg C, 4 h

With lithium aluminium tetrahydride; potassium hexamethylsilazane; potassium carbonate; 18-crown-6 ether; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; toluene;

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

upstream raw materials:

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

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

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

[(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

Phenyl-carbamic acid (2R,3S)-3-[(R)-tert-butoxycarbonylamino-(4-methoxy-phenyl)-methyl]-oxiranylmethyl ester

[(1R,2S)-2-Hydroxy-1-(4-methoxy-phenyl)-2-((S)-2-oxo-[1,3]dioxolan-4-yl)-ethyl]-carbamic acid tert-butyl ester

[(1R,2S,3S)-2,3,4-Trihydroxy-1-(4-methoxy-phenyl)-butyl]-carbamic acid tert-butyl ester