6-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-trimethylsilanyl-4,5,6,6a-tetrahydro-1H-pentalen-2-one

Base Information

• Chemical Name: 6-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-trimethylsilanyl-4,5,6,6a-tetrahydro-1H-pentalen-2-one
• CAS No.: 793684-99-8
• Molecular Formula: C₂₆H₄₂O₃Si₂
• Molecular Weight: 458.789

Synonyms:6-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-trimethylsilanyl-4,5,6,6a-tetrahydro-1H-pentalen-2-one

Chemical Property of 6-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-trimethylsilanyl-4,5,6,6a-tetrahydro-1H-pentalen-2-one

Chemical Property:

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Technology Process of 6-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-trimethylsilanyl-4,5,6,6a-tetrahydro-1H-pentalen-2-one

There total 1 articles about 6-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-trimethylsilanyl-4,5,6,6a-tetrahydro-1H-pentalen-2-one 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: 80.0%

carbon monoxide (201230-82-2) + [(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-trimethylsilanyl-3-vinyl-hept-6-ynyloxymethyl]-benzene → 6-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-trimethylsilanyl-4,5,6,6a-tetrahydro-1H-pentalen-2-one (793684-99-8)

Guidance literature:

With dicobalt octacarbonyl; In octane; at 105 ℃; for 120h; under 22502.3 Torr;

DOI:10.1016/j.tet.2004.06.143

Reference yield:

6-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-trimethylsilanyl-4,5,6,6a-tetrahydro-1H-pentalen-2-one (793684-99-8) → Thiocarbonic acid O-[(1S,2R,3aS,6aR)-1-((R)-5-methoxy-heptyl)-5-oxo-octahydro-pentalen-2-yl] ester O-phenyl ester (793685-05-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 92 percent / H₂ / Pd/BaSO₄ / ethyl acetate / 0 °C / 750.08 Torr

2.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 90 percent / n-BuLi; AgCl / hexane; tetrahydrofuran / 0.25 h / -78 °C

4.1: H₂; AcOH / Pd/C / 6 h / 2250.23 Torr

4.2: 84 percent / aq. AcOH / 15 h / 50 °C

5.1: 90 percent / pyridine / CH₂Cl₂ / 16 h / 20 °C

With pyridine; n-butyllithium; oxalyl dichloride; hydrogen; acetic acid; dimethyl sulfoxide; triethylamine; silver(I) chloride; palladium on activated charcoal; Pd-BaSO₄; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; 2.1: Swern oxidation / 3.1: Wittig reaction;

DOI:10.1016/j.tet.2004.06.143

Reference yield:

6-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-trimethylsilanyl-4,5,6,6a-tetrahydro-1H-pentalen-2-one (793684-99-8) → cyoctol (89672-11-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 92 percent / H₂ / Pd/BaSO₄ / ethyl acetate / 0 °C / 750.08 Torr

2.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 90 percent / n-BuLi; AgCl / hexane; tetrahydrofuran / 0.25 h / -78 °C

4.1: H₂; AcOH / Pd/C / 6 h / 2250.23 Torr

4.2: 84 percent / aq. AcOH / 15 h / 50 °C

5.1: 90 percent / pyridine / CH₂Cl₂ / 16 h / 20 °C

6.1: 89 percent / (n-Bu)3SnH; AIBN / toluene / 2.5 h / 90 °C

With pyridine; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; acetic acid; dimethyl sulfoxide; triethylamine; silver(I) chloride; palladium on activated charcoal; Pd-BaSO₄; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; toluene; 2.1: Swern oxidation / 3.1: Wittig reaction / 6.1: Barton-McCombie reaction;

DOI:10.1016/j.tet.2004.06.143

upstream raw materials:

carbon monoxide

Downstream raw materials:

cyoctol

(3aR,4S,5R,6aS)-5-Hydroxy-4-((R)-5-methoxy-heptyl)-hexahydro-pentalen-2-one

Thiocarbonic acid O-[(1S,2R,3aS,6aR)-1-((R)-5-methoxy-heptyl)-5-oxo-octahydro-pentalen-2-yl] ester O-phenyl ester

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