methyl (4R,2Z)-2-bromo-5,5-dimethyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate

Base Information

• Chemical Name: methyl (4R,2Z)-2-bromo-5,5-dimethyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate
• CAS No.: 736948-11-1
• Molecular Formula: C₁₈H₂₆BrNO₄S
• Molecular Weight: 432.379

Synonyms:methyl (4R,2Z)-2-bromo-5,5-dimethyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate

Chemical Property of methyl (4R,2Z)-2-bromo-5,5-dimethyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate

Chemical Property:

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Technology Process of methyl (4R,2Z)-2-bromo-5,5-dimethyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate

There total 3 articles about methyl (4R,2Z)-2-bromo-5,5-dimethyl-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:

2-mesitylenesulphonyl chloride (773-64-8) + (Z)-(R)-4-Amino-2-bromo-5,5-dimethyl-hex-2-enoic acid methyl ester → methyl (4R,2Z)-2-bromo-5,5-dimethyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate (736948-11-1)

Guidance literature:

With triethylamine; In chloroform; at 0 ℃; for 0.5h;

DOI:10.1021/jo049663f

Reference yield:

N-Boc-L-tert-leucinol (153645-26-2,545433-63-4) → methyl (4R,2Z)-2-bromo-5,5-dimethyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate (736948-11-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / CHCl₃ / 16 h / 20 °C

2: trifluoroacetic acid / CHCl₃ / 1.5 h / 0 °C

3: 1.81 g / Et₃N / CHCl₃ / 0.5 h / 0 °C

With triethylamine; trifluoroacetic acid; In chloroform;

DOI:10.1021/jo049663f

Reference yield:

methyl (4R,2Z)-2-bromo-4-[N-(tert-butoxycarbonyl)amino]-5,5-dimethylhex-2-enoate (253675-94-4) → methyl (4R,2Z)-2-bromo-5,5-dimethyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate (736948-11-1)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / CHCl₃ / 1.5 h / 0 °C

2: 1.81 g / Et₃N / CHCl₃ / 0.5 h / 0 °C

With triethylamine; trifluoroacetic acid; In chloroform;

DOI:10.1021/jo049663f

upstream raw materials:

2-mesitylenesulphonyl chloride

N-Boc-L-tert-leucinol

methyl (4R,2Z)-2-bromo-4-[N-(tert-butoxycarbonyl)amino]-5,5-dimethylhex-2-enoate

Downstream raw materials:

(4R,2Z)-2-bromo-5,5-dimethyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enyl methylsulfonate

N-allyl-N-[(1R)-1-tert-butylbuta-2,3-dienyl]-2,4,6-trimethylphenylsulfonamide

(4R)-5,5-dimethyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hexa-1,2-diene

(4R,2Z)-2-bromo-5,5-dimethyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-en-1-ol

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