(5S)-5-[N-(tert-butyloxycarbonyl)amino]-6-phenyl-2-hexen-4-one

Base Information

• Chemical Name: (5S)-5-[N-(tert-butyloxycarbonyl)amino]-6-phenyl-2-hexen-4-one
• CAS No.: 198208-03-6
• Molecular Formula: C₁₇H₂₃NO₃
• Molecular Weight: 289.375
• Mol file: 198208-03-6.mol

Synonyms:(5S)-5-[N-(tert-butyloxycarbonyl)amino]-6-phenyl-2-hexen-4-one

Chemical Property of (5S)-5-[N-(tert-butyloxycarbonyl)amino]-6-phenyl-2-hexen-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S)-5-[N-(tert-butyloxycarbonyl)amino]-6-phenyl-2-hexen-4-one

There total 2 articles about (5S)-5-[N-(tert-butyloxycarbonyl)amino]-6-phenyl-2-hexen-4-one 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: 83.0%

acetaldehyde (75-07-0,9002-91-9) + dimethyl [(3S)-4-phenyl-3-[N-(tert-butyloxycarbonyl)amino]-2-oxobutyl]phosphonate (176504-90-8) → (5S)-5-[N-(tert-butyloxycarbonyl)amino]-6-phenyl-2-hexen-4-one (198208-03-6)

Guidance literature:

With potassium carbonate; In ethanol; for 4h;

DOI:10.1021/jo971202p

Reference yield:

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester (51987-73-6) → (5S)-5-[N-(tert-butyloxycarbonyl)amino]-6-phenyl-2-hexen-4-one (198208-03-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / -78 °C

2: 83 percent / K₂CO₃ / ethanol / 4 h

With potassium carbonate; In tetrahydrofuran; ethanol;

DOI:10.1021/jo971202p

Reference yield: 48.0%

(5S)-5-[N-(tert-butyloxycarbonyl)amino]-6-phenyl-2-hexen-4-one (198208-03-6) → (4R,5S)-5-[N-(tert-butyloxycarbonyl)amino]-4-hydroxy-6-phenyl-2-hexene (198208-10-5) + (4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-4-hydroxy-6-phenyl-2-hexene

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h; Yields of byproduct given;

DOI:10.1021/jo971202p

upstream raw materials:

acetaldehyde

dimethyl [(3S)-4-phenyl-3-[N-(tert-butyloxycarbonyl)amino]-2-oxobutyl]phosphonate

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

Downstream raw materials:

(4R,5S)-5-[N-(tert-butyloxycarbonyl)amino]-4-hydroxy-6-phenyl-2-hexene