(5S)-2,6-dimethyl-5-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-2,3-heptadiene

Base Information

• Chemical Name: (5S)-2,6-dimethyl-5-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-2,3-heptadiene
• CAS No.: 220765-24-2
• Molecular Formula: C₁₈H₂₇NO₂S
• Molecular Weight: 321.484

Synonyms:(5S)-2,6-dimethyl-5-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-2,3-heptadiene

Chemical Property of (5S)-2,6-dimethyl-5-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-2,3-heptadiene

Chemical Property:

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Technology Process of (5S)-2,6-dimethyl-5-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-2,3-heptadiene

There total 2 articles about (5S)-2,6-dimethyl-5-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-2,3-heptadiene 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:

methyllithium (917-54-4) + (2R,3S)-2-ethynyl-3-isopropyl-N-(2,4,6-trimethyl-phenylsulfonyl)-aziridine (220765-18-4) → (5S,aR)-6-methyl-5-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-2,3-heptadiene + (5S,aS)-6-methyl-5-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-2,3-heptadiene + (5S)-2,6-dimethyl-5-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-2,3-heptadiene (220765-24-2)

Guidance literature:

methyllithium; With lithium chloride; lithium bromide; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; for 0.166667h;

(2R,3S)-2-ethynyl-3-isopropyl-N-(2,4,6-trimethyl-phenylsulfonyl)-aziridine; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4020(00)00136-8

Reference yield:

(2R,3S)-2-ethynyl-3-isopropyl-N-(2,4,6-trimethyl-phenylsulfonyl)-aziridine (220765-18-4) → (5S,aR)-6-methyl-5-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-2,3-heptadiene + (5S,aS)-6-methyl-5-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-2,3-heptadiene + (5S)-2,6-dimethyl-5-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-2,3-heptadiene (220765-24-2)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 0.5h; Yield given; Yields of byproduct given;

DOI:10.1016/S0040-4039(98)02348-X

Reference yield: 89.0%

Cinnamyl bromide (4392-24-9) + (5S)-2,6-dimethyl-5-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-2,3-heptadiene (220765-24-2) → N-[(1S)-1-isopropyl-4-methylpenta-2,3-dienyl]-2,4,6-trimethyl-N-[(E)-3-phenylprop-2-enyl]-phenylsulfonamide

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1021/jo0700528

upstream raw materials:

(2R,3S)-2-ethynyl-3-isopropyl-N-(2,4,6-trimethyl-phenylsulfonyl)-aziridine

methyllithium

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