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

Base Information

• Chemical Name: (4R,5S)-5-[N-(tert-butyloxycarbonyl)amino]-4-hydroxy-6-phenyl-2-hexene
• CAS No.: 198208-10-5
• Molecular Formula: C₁₇H₂₅NO₃
• Molecular Weight: 291.39
• Mol file: 198208-10-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (4R,5S)-5-[N-(tert-butyloxycarbonyl)amino]-4-hydroxy-6-phenyl-2-hexene 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: 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

Reference yield:

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester (51987-73-6) → (4R,5S)-5-[N-(tert-butyloxycarbonyl)amino]-4-hydroxy-6-phenyl-2-hexene (198208-10-5)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / -78 °C

2: 83 percent / K₂CO₃ / ethanol / 4 h

3: 48 percent / NaBH₄ / methanol / 1 h / 0 °C

With sodium tetrahydroborate; potassium carbonate; In tetrahydrofuran; methanol; ethanol;

DOI:10.1021/jo971202p

Reference yield:

dimethyl [(3S)-4-phenyl-3-[N-(tert-butyloxycarbonyl)amino]-2-oxobutyl]phosphonate (176504-90-8) → (4R,5S)-5-[N-(tert-butyloxycarbonyl)amino]-4-hydroxy-6-phenyl-2-hexene (198208-10-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / K₂CO₃ / ethanol / 4 h

2: 48 percent / NaBH₄ / methanol / 1 h / 0 °C

With sodium tetrahydroborate; potassium carbonate; In methanol; ethanol;

DOI:10.1021/jo971202p

upstream raw materials:

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

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

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