5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-8b-hydroxy-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,5,5a,7,8,8a,8b-octahydro-imidazo[4,5-e]isoindole-2,6-dione

Base Information

• Chemical Name: 5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-8b-hydroxy-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,5,5a,7,8,8a,8b-octahydro-imidazo[4,5-e]isoindole-2,6-dione
• CAS No.: 852615-11-3
• Molecular Formula: C₆₁H₇₉N₃O₁₁S₂Si₂
• Molecular Weight: 1150.61
• Mol file: 852615-11-3.mol

Synonyms:5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-8b-hydroxy-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,5,5a,7,8,8a,8b-octahydro-imidazo[4,5-e]isoindole-2,6-dione

Chemical Property of 5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-8b-hydroxy-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,5,5a,7,8,8a,8b-octahydro-imidazo[4,5-e]isoindole-2,6-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-8b-hydroxy-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,5,5a,7,8,8a,8b-octahydro-imidazo[4,5-e]isoindole-2,6-dione

There total 32 articles about 5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-8b-hydroxy-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,5,5a,7,8,8a,8b-octahydro-imidazo[4,5-e]isoindole-2,6-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:

(S)-Pyroglutaminol (17342-08-4) → 5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-8b-hydroxy-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,5,5a,7,8,8a,8b-octahydro-imidazo[4,5-e]isoindole-2,6-dione (852615-11-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 66 percent / imidazole / dimethylformamide

2.1: 90 percent / NaHMDS / tetrahydrofuran

3.1: LiHMDS / tetrahydrofuran / -78 °C

3.2: tetrahydrofuran / -78 °C

3.3: 74 percent / H₂O₂ / ethyl acetate / 0 °C

4.1: 2,6-lutidine / benzene / 1 h / 160 °C / microwave irradiation

4.2: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂

5.1: dimethyldioxirane; magnesium sulfate / CH₂Cl₂; acetone / 3 h / -50 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium hexamethyldisilazane; 3,3-dimethyldioxirane; magnesium sulfate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; benzene; 4.1: Diels-Alder reaction;

DOI:10.1016/j.tet.2005.12.068

Reference yield:

2-oxo-1-[2-(toluene-4-sulfonyl)-vinyl]-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester (852615-18-0) → 5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-8b-hydroxy-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,5,5a,7,8,8a,8b-octahydro-imidazo[4,5-e]isoindole-2,6-dione (852615-11-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 99 percent / potassium carbonate / dimethylformamide / 16 h / 60 °C

2.1: DIBAl-H

3.1: activated manganese dioxide / CH₂Cl₂

4.1: NaH / tetrahydrofuran / 0 - 25 °C

4.2: tetrahydrofuran / 2 h

5.1: DIBAl-H / CH₂Cl₂ / -78 °C

6.1: 2,6-lutidine / benzene / 1 h / 160 °C / microwave irradiation

6.2: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂

7.1: dimethyldioxirane; magnesium sulfate / CH₂Cl₂; acetone / 3 h / -50 °C

With 2,6-dimethylpyridine; manganese(IV) oxide; 3,3-dimethyldioxirane; sodium hydride; diisobutylaluminium hydride; magnesium sulfate; potassium carbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; benzene; 4.2: Horner-Wadsworth-Emmons reaction / 6.1: Diels-Alder reaction;

DOI:10.1016/j.tet.2005.12.068

Reference yield:

3-(3,4-dimethoxybenzyl)-2-oxo-1-[2-(toluene-4-sulfonyl)-vinyl]-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester → 5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-8b-hydroxy-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,5,5a,7,8,8a,8b-octahydro-imidazo[4,5-e]isoindole-2,6-dione (852615-11-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: DIBAl-H

2.1: activated manganese dioxide / CH₂Cl₂

3.1: NaH / tetrahydrofuran / 0 - 25 °C

3.2: tetrahydrofuran / 2 h

4.1: DIBAl-H / CH₂Cl₂ / -78 °C

5.1: 2,6-lutidine / benzene / 1 h / 160 °C / microwave irradiation

5.2: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂

6.1: dimethyldioxirane; magnesium sulfate / CH₂Cl₂; acetone / 3 h / -50 °C

With 2,6-dimethylpyridine; manganese(IV) oxide; 3,3-dimethyldioxirane; sodium hydride; diisobutylaluminium hydride; magnesium sulfate; In tetrahydrofuran; dichloromethane; acetone; benzene; 3.2: Horner-Wadsworth-Emmons reaction / 5.1: Diels-Alder reaction;

DOI:10.1016/j.tet.2005.12.068

upstream raw materials:

5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

2-oxo-1-[2-(toluene-4-sulfonyl)-vinyl]-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester

2-oxo-1-[2-(toluene-4-sulfonyl)-ethyl]-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester

3-(3,4-dimethoxybenzyl)-2-oxo-1-[2-(toluene-4-sulfonyl)-ethyl]-2,3-dihydro-1H-imidazole-4-carbaldehyde

Downstream raw materials:

C₆₁H₇₈ClN₃O₁₁S₂Si₂

Refernces

• 1、 Dransfield, Paul J.,Wang, Shaohui,Dilley, Anja,Romo, Daniel. "Highly regioselective diels-alder reactions toward oroidin alkaloids: Use of a tosylvinyl moiety as a nitrogen masking group with adjustable electronics". . p. 1679 - 1682. Retrieved 2007/10/03.