3,9-bis-benzenesulfonyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-3,9-diaza-cyclopenta[d]naphthalene-5,10-dione

Base Information

• Chemical Name: 3,9-bis-benzenesulfonyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-3,9-diaza-cyclopenta[d]naphthalene-5,10-dione
• CAS No.: 244074-49-5
• Molecular Formula: C₄₀H₄₄N₂O₇S₂Si
• Molecular Weight: 757.016
• Mol file: 244074-49-5.mol

Synonyms:

Chemical Property of 3,9-bis-benzenesulfonyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-3,9-diaza-cyclopenta[d]naphthalene-5,10-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,9-bis-benzenesulfonyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-3,9-diaza-cyclopenta[d]naphthalene-5,10-dione

There total 14 articles about 3,9-bis-benzenesulfonyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-3,9-diaza-cyclopenta[d]naphthalene-5,10-dione 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:

1-Benzenesulfonyl-3,4,5,6-tetrahydropyridin-2-one (7744-25-4) → 3,9-bis-benzenesulfonyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-3,9-diaza-cyclopenta[d]naphthalene-5,10-dione (244074-49-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 73 percent / LiN(TMS)2 / tetrahydrofuran / 11 h / -60 °C

2: LiN(TMS)2 / tetrahydrofuran / 2 h / -60 °C

3: n-Bu₃SnH, AIBN / benzene / 0.5 h / Heating

4: KN(TMS)2 / tetrahydrofuran / -30 °C

5: mCPBA / CH₂Cl₂

6: various solvent(s) / 20 h / 180 °C

7: PPTS / CH₂Cl₂

8: 21 percent / HCl / tetrahydrofuran / 2 h / Heating

9: HCl

10: imidazole / dimethylformamide / 2 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(98)80033-6

Reference yield:

methyl N-benzenesulfonyl-L-serinate (221526-66-5) → 3,9-bis-benzenesulfonyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-3,9-diaza-cyclopenta[d]naphthalene-5,10-dione (244074-49-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 90 percent / p-TsOH / benzene / 3 h / Ambient temperature

2: 92 percent / DIBAL-H / toluene / 2 h / -78 °C

3: 73 percent / LiN(TMS)2 / tetrahydrofuran / 11 h / -60 °C

4: LiN(TMS)2 / tetrahydrofuran / 2 h / -60 °C

5: n-Bu₃SnH, AIBN / benzene / 0.5 h / Heating

6: KN(TMS)2 / tetrahydrofuran / -30 °C

7: mCPBA / CH₂Cl₂

8: various solvent(s) / 20 h / 180 °C

9: PPTS / CH₂Cl₂

10: 21 percent / HCl / tetrahydrofuran / 2 h / Heating

11: HCl

12: imidazole / dimethylformamide / 2 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4039(98)80033-6

Reference yield:

(S)-3-Benzenesulfonyl-2,2-dimethyl-oxazolidine-4-carboxylic acid (637773-08-1) → 3,9-bis-benzenesulfonyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-3,9-diaza-cyclopenta[d]naphthalene-5,10-dione (244074-49-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 73 percent / LiN(TMS)2 / tetrahydrofuran / 11 h / -60 °C

2: LiN(TMS)2 / tetrahydrofuran / 2 h / -60 °C

3: n-Bu₃SnH, AIBN / benzene / 0.5 h / Heating

4: KN(TMS)2 / tetrahydrofuran / -30 °C

5: mCPBA / CH₂Cl₂

6: various solvent(s) / 20 h / 180 °C

7: PPTS / CH₂Cl₂

8: 21 percent / HCl / tetrahydrofuran / 2 h / Heating

9: HCl

10: imidazole / dimethylformamide / 2 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(98)80033-6

upstream raw materials:

tert-butylchlorodiphenylsilane

(4aS,7aS,9R,10aS)-2,8-Bis-benzenesulfonyl-9-hydroxymethyl-octahydro-pyrrolo[2,3-i]isoquinoline-1,6-dione

1-Benzenesulfonyl-3,4,5,6-tetrahydropyridin-2-one

methyl N-benzenesulfonyl-L-serinate

Downstream raw materials:

C₄₂H₄₈N₂O₈S₂Si

C₃₆H₄₄N₂O₆SSi

C₃₅H₄₈N₂O₆Si