(S)-N-{(4-tolyl)(oxido)[((1S,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)amino]-λ⁴-sulfanylidene}tosylamide

Base Information

• Chemical Name: (S)-N-{(4-tolyl)(oxido)[((1S,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)amino]-λ⁴-sulfanylidene}tosylamide
• CAS No.: 1259394-51-8
• Molecular Formula: C₂₄H₃₀N₂O₃S₂
• Molecular Weight: 458.646
• Mol file: 1259394-51-8.mol

Synonyms:(S)-N-{(4-tolyl)(oxido)[((1S,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)amino]-λ⁴-sulfanylidene}tosylamide

Chemical Property of (S)-N-{(4-tolyl)(oxido)[((1S,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)amino]-λ⁴-sulfanylidene}tosylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-{(4-tolyl)(oxido)[((1S,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)amino]-λ⁴-sulfanylidene}tosylamide

There total 10 articles about (S)-N-{(4-tolyl)(oxido)[((1S,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)amino]-λ⁴-sulfanylidene}tosylamide 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: 71.0%

N-[(1S)-amino(4-tolyl)oxido-λ4-sulfanylidene]tosylamide (816444-61-8) + (-)-α-pinene (7785-26-4,25766-18-1) → (S)-N-{(4-tolyl)(oxido)[((1S,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)amino]-λ4-sulfanylidene}tosylamide (1259394-51-8)

Guidance literature:

With Rh₂{(S)-nta}4; bis(tertbutylcarbonyloxy)iodobenzene; In methanol; 1,1,2,2-tetrachloroethane; at -35 ℃; for 72h; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1039/c0dt00283f

Reference yield:

N-[(1S)-amino(4-tolyl)oxido-λ4-sulfanylidene]tosylamide (816444-61-8) + rac-α-pinene (80-56-8,25766-18-1) → (S)-N-{(4-tolyl)(oxido)[((1S,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)amino]-λ4-sulfanylidene}tosylamide (1259394-51-8) + (S)-N-{(4-tolyl)(oxido)[((1S,2S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)amino]-λ4-sulfanylidene}tosylamide (1396021-11-6)

Guidance literature:

With dirhodium tetrakis{(2S)-2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoic acid}; bis(tertbutylcarbonyloxy)iodobenzene; In methanol; 1,2-dichloro-ethane; at -35 ℃; for 72h; Overall yield = 89 %; Overall yield = 812 mg; diastereoselective reaction; Molecular sieve;

DOI:10.1055/s-0033-1339280

Reference yield:

sodium 4-methylbenzenesulfinate (824-79-3) → (S)-N-{(4-tolyl)(oxido)[((1S,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)amino]-λ4-sulfanylidene}tosylamide (1259394-51-8) + (S)-N-{(4-tolyl)(oxido)[((1S,2S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)amino]-λ4-sulfanylidene}tosylamide (1396021-11-6)

Guidance literature:

Multi-step reaction with 5 steps

1: thionyl chloride / toluene / 16 h / 20 °C / Inert atmosphere

2: toluene / 4 h / 80 °C

3: sodium hydrogencarbonate / dichloromethane; water / 16 h / 0 - 20 °C

4: trifluorormethanesulfonic acid / dichloromethane / 1 h / 20 °C

5: dirhodium tetrakis{(2S)-2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoic acid}; bis(tertbutylcarbonyloxy)iodobenzene / methanol; 1,2-dichloro-ethane / 72 h / -35 °C / Molecular sieve

With thionyl chloride; trifluorormethanesulfonic acid; dirhodium tetrakis{(2S)-2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoic acid}; bis(tertbutylcarbonyloxy)iodobenzene; sodium hydrogencarbonate; In methanol; dichloromethane; water; 1,2-dichloro-ethane; toluene;

DOI:10.1055/s-0033-1339280

upstream raw materials:

N-[(1S)-amino(4-tolyl)oxido-λ⁴-sulfanylidene]tosylamide

(-)-α-pinene

N-(4-methylbenzenesulfonyl) 4-methylphenyl sulfonimidoyl chloride

chloroamine-T

Refernces

• 1、 Lescot, Camille,Darses, Benjamin,Collet, Florence,Retailleau, Pascal,Dauban, Philippe. "Intermolecular C-H amination of complex molecules: Insights into the factors governing the selectivity". . p. 7232 - 7240. Retrieved 2012/10/30.