Methyl (4S,2E)-2-bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate

Base Information

• Chemical Name: Methyl (4S,2E)-2-bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate
• CAS No.: 253675-93-3
• Molecular Formula: C₁₇H₂₄BrNO₄S
• Molecular Weight: 418.352

Synonyms:Methyl (4S,2E)-2-bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate

Chemical Property of Methyl (4S,2E)-2-bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate

Chemical Property:

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Technology Process of Methyl (4S,2E)-2-bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate

There total 2 articles about Methyl (4S,2E)-2-bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate 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:

(2S)-N-(2,4,6-trimethylbenzenesulfonyl)-2-amino-3-methyl-butanol (139192-50-0) → Methyl (4S,2E)-2-bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate (253675-93-3)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride; DMSO; diisopropylethylamine / CHCl₃; hexane / 1.5 h / -78 - 0 °C

2: CHCl₃ / 15 h / 0 °C

With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In hexane; chloroform; 1: Oxidation / 2: Condensation;

DOI:10.1039/a905027b

Reference yield:

N-((S)-1-Formyl-2-methyl-propyl)-2,4,6-trimethyl-benzenesulfonamide (148838-43-1) + methyl 2-bromo-2-(triphenylphosphanylidene)acetate (13504-77-3) → Methyl (4S,2Z)-2-bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate (220324-04-9) + Methyl (4S,2E)-2-bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate (253675-93-3)

Guidance literature:

In chloroform; at 0 ℃; for 15h;

DOI:10.1039/a905027b

Reference yield: 64.0%

Methyl (4S,2E)-2-bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate (253675-93-3) → (4S,2E)-2-bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-en-1-ol

Guidance literature:

With diisobutylaluminium hydride; In chloroform; toluene; at -78 - 0 ℃; for 2h;

DOI:10.1021/jo016320y

upstream raw materials:

N-((S)-1-Formyl-2-methyl-propyl)-2,4,6-trimethyl-benzenesulfonamide

methyl 2-bromo-2-(triphenylphosphanylidene)acetate

(2S)-N-(2,4,6-trimethylbenzenesulfonyl)-2-amino-3-methyl-butanol

Downstream raw materials:

(4S)-5-methyl-4-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-1,2-hexadiene

(4S,2E)-2-bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-en-1-yl methyl-sulfonate

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