(-)-(1R,3R,5S)-5-(N-allyl-N-(4-methylbenzenesulfonyl)amino)-3-(tert-butyl-dimethylsilanyloxy)cyclohept-6-enol

Base Information

• Chemical Name: (-)-(1R,3R,5S)-5-(N-allyl-N-(4-methylbenzenesulfonyl)amino)-3-(tert-butyl-dimethylsilanyloxy)cyclohept-6-enol
• CAS No.: 466645-78-3
• Molecular Formula: C₂₃H₃₇NO₄SSi
• Molecular Weight: 451.703
• Mol file: 466645-78-3.mol

Synonyms:(-)-(1R,3R,5S)-5-(N-allyl-N-(4-methylbenzenesulfonyl)amino)-3-(tert-butyl-dimethylsilanyloxy)cyclohept-6-enol

Chemical Property of (-)-(1R,3R,5S)-5-(N-allyl-N-(4-methylbenzenesulfonyl)amino)-3-(tert-butyl-dimethylsilanyloxy)cyclohept-6-enol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1R,3R,5S)-5-(N-allyl-N-(4-methylbenzenesulfonyl)amino)-3-(tert-butyl-dimethylsilanyloxy)cyclohept-6-enol

There total 1 articles about (-)-(1R,3R,5S)-5-(N-allyl-N-(4-methylbenzenesulfonyl)amino)-3-(tert-butyl-dimethylsilanyloxy)cyclohept-6-enol 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: 82.0%

4-methyl-N-(2-propenyl)benzenesulfonamide (50487-71-3) + (1R,4S,6S)-4-acetoxy-6-[(tert-butyldimethylsilyl)oxy]-2-cyclohepten-1-ol (134734-52-4) → (-)-(1R,3R,5S)-5-(N-allyl-N-(4-methylbenzenesulfonyl)amino)-3-(tert-butyl-dimethylsilanyloxy)cyclohept-6-enol (466645-78-3)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium hydride; 1,4-di(diphenylphosphino)-butane; In tetrahydrofuran; N,N-dimethyl-formamide; at 50 ℃; for 0.5h;

DOI:10.1016/S0040-4020(02)00832-3

Reference yield: 91.0%

benzoyl chloride (98-88-4) + (-)-(1R,3R,5S)-5-(N-allyl-N-(4-methylbenzenesulfonyl)amino)-3-(tert-butyl-dimethylsilanyloxy)cyclohept-6-enol (466645-78-3) → (+)-(1R,3R,5S)-5-(N-allyl-N-(4-methylbenzenesulfonyl)amino)-3-(tert-butyl-dimethylsilanyloxy)cyclohept-6-enyl benzoate (501415-96-9)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1016/S0040-4020(02)00832-3

Reference yield:

(-)-(1R,3R,5S)-5-(N-allyl-N-(4-methylbenzenesulfonyl)amino)-3-(tert-butyl-dimethylsilanyloxy)cyclohept-6-enol (466645-78-3) → (-)-(2S)-N-(4-methylbenzenesulfonyl)-2-[(2R,4R)-4-benzoyloxy-2-(tert-butyl-dimethylsilanyloxy)hex-5-enyl]-2,5-dihydro-1H-pyrrole

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / DMAP / CH₂Cl₂ / 15 h / 20 °C

2: 92 percent / ethylene; Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 12 h / Heating

With dmap; Grubbs catalyst first generation; ethene; In dichloromethane;

DOI:10.1016/S0040-4020(02)00832-3

upstream raw materials:

4-methyl-N-(2-propenyl)benzenesulfonamide

(1R,4S,6S)-4-acetoxy-6-[(tert-butyldimethylsilyl)oxy]-2-cyclohepten-1-ol

Downstream raw materials:

(+)-(1R,3R,5S)-5-(N-allyl-N-(4-methylbenzenesulfonyl)amino)-3-(tert-butyl-dimethylsilanyloxy)cyclohept-6-enyl benzoate