(4S,2E)-O-methoxycarbonyl-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol

Base Information

• Chemical Name: (4S,2E)-O-methoxycarbonyl-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol
• CAS No.: 678166-38-6
• Molecular Formula: C₂₃H₂₉NO₅S
• Molecular Weight: 431.553
• Mol file: 678166-38-6.mol

Synonyms:(4S,2E)-O-methoxycarbonyl-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol

Chemical Property of (4S,2E)-O-methoxycarbonyl-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,2E)-O-methoxycarbonyl-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol

There total 4 articles about (4S,2E)-O-methoxycarbonyl-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol 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%

methyl chloroformate (79-22-1) + (4S,2E)-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol (678166-33-1) → (4S,2E)-O-methoxycarbonyl-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol (678166-38-6)

Guidance literature:

With pyridine; In tetrahydrofuran; chloroform; at -78 - 0 ℃;

DOI:10.1248/cpb.52.111

Reference yield:

(S)-N-(2,4,6-trimethylphenylsulfonyl)phenylalaninol (182880-90-6) → (4S,2E)-O-methoxycarbonyl-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol (678166-38-6)

Guidance literature:

Multi-step reaction with 4 steps

1: (COCl)2; DMSO; diisopropylethylamine / CHCl₃; CH₂Cl₂ / 0.5 h / -78 °C

2: 3.56 g / CHCl₃ / 18 h / 0 °C

3: 99 percent / DIBAL-H / CHCl₃; toluene / 1 h / -78 °C

4: 87 percent / pyridine / CHCl₃; tetrahydrofuran / -78 - 0 °C

With pyridine; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; chloroform; toluene; 1: Swern oxidation;

DOI:10.1248/cpb.52.111

Reference yield:

N-((S)-1-Formyl-2-phenyl-ethyl)-2,4,6-trimethyl-benzenesulfonamide (220324-31-2) → (4S,2E)-O-methoxycarbonyl-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol (678166-38-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 3.56 g / CHCl₃ / 18 h / 0 °C

2: 99 percent / DIBAL-H / CHCl₃; toluene / 1 h / -78 °C

3: 87 percent / pyridine / CHCl₃; tetrahydrofuran / -78 - 0 °C

With pyridine; diisobutylaluminium hydride; In tetrahydrofuran; chloroform; toluene;

DOI:10.1248/cpb.52.111

upstream raw materials:

methyl chloroformate

(4S,2E)-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol

(S)-N-(2,4,6-trimethylphenylsulfonyl)phenylalaninol

N-((S)-1-Formyl-2-phenyl-ethyl)-2,4,6-trimethyl-benzenesulfonamide