[(E)-(1R,2R)-4-Benzenesulfonyl-8-(2,5-bis-benzyloxy-phenyl)-2,6-dimethyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-oct-6-enyloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(E)-(1R,2R)-4-Benzenesulfonyl-8-(2,5-bis-benzyloxy-phenyl)-2,6-dimethyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-oct-6-enyloxy]-tert-butyl-dimethyl-silane
• CAS No.: 378198-07-3
• Molecular Formula: C₅₇H₇₈O₅SSi
• Molecular Weight: 903.395
• Mol file: 378198-07-3.mol

Synonyms:[(E)-(1R,2R)-4-Benzenesulfonyl-8-(2,5-bis-benzyloxy-phenyl)-2,6-dimethyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-oct-6-enyloxy]-tert-butyl-dimethyl-silane

Chemical Property of [(E)-(1R,2R)-4-Benzenesulfonyl-8-(2,5-bis-benzyloxy-phenyl)-2,6-dimethyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-oct-6-enyloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(E)-(1R,2R)-4-Benzenesulfonyl-8-(2,5-bis-benzyloxy-phenyl)-2,6-dimethyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-oct-6-enyloxy]-tert-butyl-dimethyl-silane

There total 21 articles about [(E)-(1R,2R)-4-Benzenesulfonyl-8-(2,5-bis-benzyloxy-phenyl)-2,6-dimethyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-oct-6-enyloxy]-tert-butyl-dimethyl-silane 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: 76.0%

2-[(E)-4-bromo-3-methyl-2-butenyl]-1,4-dibenzyloxybenzene (378198-06-2) + [(1R,2R)-4-Benzenesulfonyl-2-methyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-butoxy]-tert-butyl-dimethyl-silane (378198-03-9) → [(E)-(1R,2R)-4-Benzenesulfonyl-8-(2,5-bis-benzyloxy-phenyl)-2,6-dimethyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-oct-6-enyloxy]-tert-butyl-dimethyl-silane (378198-07-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 0 ℃; for 4h;

DOI:10.1021/jo010154c

Reference yield:

(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (38419-75-9) → [(E)-(1R,2R)-4-Benzenesulfonyl-8-(2,5-bis-benzyloxy-phenyl)-2,6-dimethyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-oct-6-enyloxy]-tert-butyl-dimethyl-silane (378198-07-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 99 percent / imidazole / dimethylformamide / 1 h / 20 °C

2.1: SOCl₂; 4-DMAP / pyridine / -50 - 0 °C

2.2: 62 percent / SeO₂; salicylic acid; tBuOOH / CH₂Cl₂ / 48 h / 20 °C

3.1: 17 percent / H₂ / Pd/C / ethanol / 12 h / 20 °C / 760.05 Torr

4.1: 98 percent / TBAF / tetrahydrofuran / 1 h / Heating

5.1: 96 percent / Et₃N; SO₃*Py / dimethylsulfoxide / 1 h / 20 °C

6.1: 87 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - 0 °C

7.1: 98 percent / AlMe₃ / toluene; CH₂Cl₂ / 24 h / 0 - 20 °C

8.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / -78 - -10 °C

9.1: 99 percent / DIBALH / tetrahydrofuran / 0.5 h / -78 °C

10.1: 70 percent / NaH / tetrahydrofuran / 2 h / 20 °C

11.1: 92 percent / NiCl₂*xH₂O; NaBH₄ / methanol / 3 h / 0 °C

12.1: 76 percent / LDA / tetrahydrofuran / 4 h / -78 - 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; thionyl chloride; pyridine-SO₃ complex; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; triethylamine; nickel dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo010154c

Reference yield:

(3aR)-(+)-sclareolide (564-20-5,1216-84-8,30450-17-0,58976-28-6,64090-92-2,67844-42-2,79768-41-5,79768-42-6,86688-27-9,86688-28-0,95406-08-9,98719-44-9,98719-46-1,131831-65-7,140851-80-5) → [(E)-(1R,2R)-4-Benzenesulfonyl-8-(2,5-bis-benzyloxy-phenyl)-2,6-dimethyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-oct-6-enyloxy]-tert-butyl-dimethyl-silane (378198-07-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

2.1: 99 percent / imidazole / dimethylformamide / 1 h / 20 °C

3.1: SOCl₂; 4-DMAP / pyridine / -50 - 0 °C

3.2: 62 percent / SeO₂; salicylic acid; tBuOOH / CH₂Cl₂ / 48 h / 20 °C

4.1: 17 percent / H₂ / Pd/C / ethanol / 12 h / 20 °C / 760.05 Torr

5.1: 98 percent / TBAF / tetrahydrofuran / 1 h / Heating

6.1: 96 percent / Et₃N; SO₃*Py / dimethylsulfoxide / 1 h / 20 °C

7.1: 87 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - 0 °C

8.1: 98 percent / AlMe₃ / toluene; CH₂Cl₂ / 24 h / 0 - 20 °C

9.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / -78 - -10 °C

10.1: 99 percent / DIBALH / tetrahydrofuran / 0.5 h / -78 °C

11.1: 70 percent / NaH / tetrahydrofuran / 2 h / 20 °C

12.1: 92 percent / NiCl₂*xH₂O; NaBH₄ / methanol / 3 h / 0 °C

13.1: 76 percent / LDA / tetrahydrofuran / 4 h / -78 - 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; thionyl chloride; pyridine-SO₃ complex; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; triethylamine; nickel dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo010154c

upstream raw materials:

2-[(E)-4-bromo-3-methyl-2-butenyl]-1,4-dibenzyloxybenzene

[(1R,2R)-4-Benzenesulfonyl-2-methyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-butoxy]-tert-butyl-dimethyl-silane

(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

prenylhydroquinone

Downstream raw materials:

(2R,3R,7E)-9-(2,5-dibenzyloxyphenyl)-3,7-dimethyl-1-[(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-7-nonen-2-ol

(2R,3R,7E)-9-(2,5-dihydroxyphenyl)-3,7-dimethyl-1-[(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-7-nonen-2-ol

2-[(E)-(7R,8R)-8-Hydroxy-3,7-dimethyl-9-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-non-2-enyl]-[1,4]benzoquinone

(2R,3R,7E)-2-(tert-butyldimethylsiliyloxy)-9-(2,5-dibenzyloxyphenyl)-3,7-dimethyl-1-[(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-7-nonene

Refernces