(E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenyl-2-pentenyl methanesulfonate

Base Information

• Chemical Name: (E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenyl-2-pentenyl methanesulfonate
• CAS No.: 188000-27-3
• Molecular Formula: C₁₇H₂₅NO₅S
• Molecular Weight: 355.455
• Mol file: 188000-27-3.mol

Synonyms:(E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenyl-2-pentenyl methanesulfonate

Chemical Property of (E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenyl-2-pentenyl methanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenyl-2-pentenyl methanesulfonate

There total 1 articles about (E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenyl-2-pentenyl methanesulfonate 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: 91.0%

(4S)-4-(N-tert-butoxycarbonyl)amino-5-phenyl-2-penten-1-ol (124818-93-5) + methanesulfonyl chloride (124-63-0) → (E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenyl-2-pentenyl methanesulfonate (188000-27-3)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(02)00026-1

Reference yield: 87.0%

potassium thioacyanate (333-20-0) + (E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenyl-2-pentenyl methanesulfonate (188000-27-3) → tert-butyl N-[(1S,2E)-1-benzyl-4-thiocyanato-2-butenyl]carbamate (188000-32-0)

Guidance literature:

In acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(02)00026-1

Reference yield:

(E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenyl-2-pentenyl methanesulfonate (188000-27-3) → (4S,5S)-4-vinyl-5-benzyltetrahydro-1H-2-imidazolethione

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / acetonitrile / 2 h / 20 °C

2: 85 percent / 2-hydroxypyridine / xylene / 3 h / 80 °C

3: 94 percent / trifluoroacetic acid; water / 0.25 h / 20 °C

With 2-hydroxypyridin; water; trifluoroacetic acid; In acetonitrile; xylene;

DOI:10.1016/S0040-4020(02)00026-1

upstream raw materials:

(4S)-4-(N-tert-butoxycarbonyl)amino-5-phenyl-2-penten-1-ol

methanesulfonyl chloride

Downstream raw materials:

tert-butyl N-[(1S,2E)-1-benzyl-4-thiocyanato-2-butenyl]carbamate

(4S,5S)-5-ethenyl-4-phenylmethyloxazolidin-2-one

(4S,5R)-5-ethenyl-4-phenylmethyloxazolidin-2-one

tert-butyl (4S,5S)-5-benzyl-2-thioxo-4-vinyltetrahydro-1H-1-imidazolecarboxylate