(S,Z)-bis(1,1-dimethylethyl) N-(1-methyl-4-phenylbut-2-enyl)-imidodicarbonate

Base Information

• Chemical Name: (S,Z)-bis(1,1-dimethylethyl) N-(1-methyl-4-phenylbut-2-enyl)-imidodicarbonate
• CAS No.: 172472-87-6
• Molecular Formula: C₂₁H₃₁NO₄
• Molecular Weight: 361.481
• Mol file: 172472-87-6.mol

Synonyms:(S,Z)-bis(1,1-dimethylethyl) N-(1-methyl-4-phenylbut-2-enyl)-imidodicarbonate

Chemical Property of (S,Z)-bis(1,1-dimethylethyl) N-(1-methyl-4-phenylbut-2-enyl)-imidodicarbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,Z)-bis(1,1-dimethylethyl) N-(1-methyl-4-phenylbut-2-enyl)-imidodicarbonate

There total 1 articles about (S,Z)-bis(1,1-dimethylethyl) N-(1-methyl-4-phenylbut-2-enyl)-imidodicarbonate 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: 87.0%

di-tert-butyl dicarbonate (24424-99-5) + (RS,Z)-1,1-dimethylethyl N-(1-methyl-4-phenylbut-2-enyl)-carbamate → (R,Z)-bis(1,1-dimethylethyl) N-(1-methyl-4-phenylbut-2-enyl)-imidodicarbonate + (S,Z)-bis(1,1-dimethylethyl) N-(1-methyl-4-phenylbut-2-enyl)-imidodicarbonate (172472-87-6)

Guidance literature:

With n-butyllithium; In diethyl ether; hexane; Yields of byproduct given. Title compound not separated from byproducts; 1.) 0 deg C, 5 min; 2.) r.t., 10 min;

DOI:10.1055/s-1995-4071

Reference yield:

(S,Z)-bis(1,1-dimethylethyl) N-(1-methyl-4-phenylbut-2-enyl)-imidodicarbonate (172472-87-6) → (1R,2S)-(E)-bis(1,1-dimethylethyl) N-(hydroperoxy-1-methyl-4-phenylbut-3-enyl)imidodicarbonate + (1S,2R)-(E)-bis(1,1-dimethylethyl) N-(hydroperoxy-1-methyl-4-phenylbut-3-enyl)imidodicarbonate (172472-88-7)

Guidance literature:

With oxygen; In tetrachloromethane; at -25 ℃; for 5h; Title compound not separated from byproducts; Irradiation;

DOI:10.1111/j.1751-1097.1999.tb08241.x

Reference yield:

(S,Z)-bis(1,1-dimethylethyl) N-(1-methyl-4-phenylbut-2-enyl)-imidodicarbonate (172472-87-6) → (3R,4S)-4-Amino-1-phenyl-1-penten-3-ol (107673-74-5,96861-89-1)

Guidance literature:

Multi-step reaction with 3 steps

1: O₂ / CCl₄ / 5 h / -25 °C / Irradiation

2: 62 percent / PPh₃ / CCl₄ / 0.08 h / -25 °C

3: 89 percent / aq. KOH / methanol / 6 h / 90 °C

With potassium hydroxide; oxygen; triphenylphosphine; In methanol; tetrachloromethane; 1: Oxidation / 2: Reduction / 3: Hydrolysis;

DOI:10.1111/j.1751-1097.1999.tb08241.x

upstream raw materials:

di-tert-butyl dicarbonate

Downstream raw materials:

(1S,2R)-(E)-bis(1,1-dimethylethyl) N-(hydroperoxy-1-methyl-4-phenylbut-3-enyl)imidodicarbonate

(3R,4S)-4-Amino-1-phenyl-1-penten-3-ol

(1S,2R,E)-bis(1,1-dimethylethyl) N-(2-hydroxy-1-methyl-4-phenylbut-3-enyl)imidodicarbonate