<6aR*-(6aβ,9α,10aα)>-2,6,6a,7,8,9,10,10a-octahydro-6,6,9-trimethyl-10-oxo-2-p-toluenesulfonyl-9-vinylnaphth<1,2,3-cd>indole

Base Information

• Chemical Name: <6aR*-(6aβ,9α,10aα)>-2,6,6a,7,8,9,10,10a-octahydro-6,6,9-trimethyl-10-oxo-2-p-toluenesulfonyl-9-vinylnaphth<1,2,3-cd>indole
• CAS No.: 131572-86-6
• Molecular Formula: C₂₇H₂₉NO₃S
• Molecular Weight: 447.598
• Mol file: 131572-86-6.mol

Synonyms:

Chemical Property of <6aR*-(6aβ,9α,10aα)>-2,6,6a,7,8,9,10,10a-octahydro-6,6,9-trimethyl-10-oxo-2-p-toluenesulfonyl-9-vinylnaphth<1,2,3-cd>indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <6aR*-(6aβ,9α,10aα)>-2,6,6a,7,8,9,10,10a-octahydro-6,6,9-trimethyl-10-oxo-2-p-toluenesulfonyl-9-vinylnaphth<1,2,3-cd>indole

There total 6 articles about <6aR*-(6aβ,9α,10aα)>-2,6,6a,7,8,9,10,10a-octahydro-6,6,9-trimethyl-10-oxo-2-p-toluenesulfonyl-9-vinylnaphth<1,2,3-cd>indole 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: 68.0%

<6aR*-(6aβ,9α,10β,10aβ)>-2,6,6a,7,8,9,10,10a-octahydro-10-hydroxy-6,6,9-trimethyl-2-p-toluenesulfonyl-9-vinylnaphth<1,2,3-cd>indole (131572-85-5,131616-29-0,131616-32-5,131616-35-8,131616-36-9,131681-86-2) → <6aR*-(6aβ,9α,10aβ)>-2,6,6a,7,8,9,10,10a-octahydro-6,6,9-trimethyl-10-oxo-2-p-toluenesulfonyl-9-vinylnaphth<1,2,3-cd>indole (131572-86-6,131616-30-3,131616-31-4)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 0.666667h; Ambient temperature;

DOI:10.1016/S0040-4020(01)96007-7

Reference yield:

2,6,6a,7,8,9-hexahydro-6ξ-hydroxy-6,6,9-trimethyl-2-p-toluenesulfonyl-9-vinylnaphth<1,2,3-cd>indole (131572-74-2,131572-80-0) → <6aS*-(6aα,9α,10aβ)>-2,6,6a,7,8,9,10,10a-octahydro-6,6,9-trimethyl-10-oxo-2-p-toluenesulfonyl-9-vinylnaphth<1,2,3-cd>indole (131572-86-6,131616-30-3,131616-31-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / 5percent H₂SO₄ / acetone; H₂O / 1) 0 deg C, 30 min, 2) r.t., 3 h

2: 15 percent / LiAlH₄ / tetrahydrofuran / 15 h / 0 deg C to r.t.

3: 1) NaH / 1) THF, DMF, -20 deg C, 2) -20 deg C

4: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -75 to -67 deg C, 20 min, 2a) -67 deg C, 5 min, 2b) -20 deg C, 30 min

With lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; water; acetone;

DOI:10.1016/S0040-4020(01)96007-7

Reference yield:

2,6,7,8,9,10-hexahydro-10ξ-hydroxy-6,6,9-trimethyl-2-p-toluenesulfonyl-9-vinylnaphth<1,2,3-cd>indole (131573-12-1) → <6aS*-(6aα,9α,10aβ)>-2,6,6a,7,8,9,10,10a-octahydro-6,6,9-trimethyl-10-oxo-2-p-toluenesulfonyl-9-vinylnaphth<1,2,3-cd>indole (131572-86-6,131616-30-3,131616-31-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 15 percent / LiAlH₄ / tetrahydrofuran / 15 h / 0 deg C to r.t.

2: 1) NaH / 1) THF, DMF, -20 deg C, 2) -20 deg C

3: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -75 to -67 deg C, 20 min, 2a) -67 deg C, 5 min, 2b) -20 deg C, 30 min

With lithium aluminium tetrahydride; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)96007-7

upstream raw materials:

<6aR*-(6aβ,9α,10β,10aβ)>-2,6,6a,7,8,9,10,10a-octahydro-10-hydroxy-6,6,9-trimethyl-2-p-toluenesulfonyl-9-vinylnaphth<1,2,3-cd>indole

Toluene-4-sulfonic acid (6aS,9R,10R,10aR)-6,6,9-trimethyl-2-(toluene-4-sulfonyl)-9-vinyl-2,6,6a,7,8,9,10,10a-octahydro-2-aza-aceanthrylen-10-yl ester

2,6,6a,7,8,9-hexahydro-6ξ-hydroxy-6,6,9-trimethyl-2-p-toluenesulfonyl-9-vinylnaphth<1,2,3-cd>indole

<6aS*-(6aα,9α,10α,10aα)>-2,6,6a,7,8,9,10,10a-octahydro-10-hydroxy-6,6,9-trimethyl-9-vinylnaphth<1,2,3-cd>indole

Downstream raw materials:

(6aS,9R,10S,10aR)-6,6,9-Trimethyl-2-(toluene-4-sulfonyl)-9-vinyl-2,6,6a,7,8,9,10,10a-octahydro-2-aza-aceanthrylen-10-ol

(6aR,9S,10R,10aR)-6,6,9-Trimethyl-2-(toluene-4-sulfonyl)-9-vinyl-2,6,6a,7,8,9,10,10a-octahydro-2-aza-aceanthrylen-10-ol

N-[(6aS,9R,10S,10aR)-6,6,9-Trimethyl-2-(toluene-4-sulfonyl)-9-vinyl-2,6,6a,7,8,9,10,10a-octahydro-2-aza-aceanthrylen-10-yl]-formamide

<6aS*-(6aα,9α,10α,10aβ)>-10-formamido-2,6,6a,7,8,9,10,10a-octahydro-6,6,9-trimethyl-2-p-toluenesulfonyl-9-vinylnaphth<1,2,3-cd>indole