tert-Butyl-[(R)-(2S,5R,2'R,5'R,2''R)-1-(dodecahydro-[2,2';5',2'']terfuran-5-yl)-pent-4-enyloxy]-diphenyl-silane

Base Information

• Chemical Name: tert-Butyl-[(R)-(2S,5R,2'R,5'R,2''R)-1-(dodecahydro-[2,2';5',2'']terfuran-5-yl)-pent-4-enyloxy]-diphenyl-silane
• CAS No.: 444884-33-7
• Molecular Formula: C₃₃H₄₆O₄Si
• Molecular Weight: 534.811

Synonyms:tert-Butyl-[(R)-(2S,5R,2'R,5'R,2''R)-1-(dodecahydro-[2,2';5',2'']terfuran-5-yl)-pent-4-enyloxy]-diphenyl-silane

Chemical Property of tert-Butyl-[(R)-(2S,5R,2'R,5'R,2''R)-1-(dodecahydro-[2,2';5',2'']terfuran-5-yl)-pent-4-enyloxy]-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-[(R)-(2S,5R,2'R,5'R,2''R)-1-(dodecahydro-[2,2';5',2'']terfuran-5-yl)-pent-4-enyloxy]-diphenyl-silane

There total 7 articles about tert-Butyl-[(R)-(2S,5R,2'R,5'R,2''R)-1-(dodecahydro-[2,2';5',2'']terfuran-5-yl)-pent-4-enyloxy]-diphenyl-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: 66.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (R)-(2S,5R,2'R,5'R,2''R)-1-(Dodecahydro-[2,2';5',2'']terfuran-5-yl)-pent-4-en-1-ol (444884-32-6) → tert-Butyl-[(R)-(2S,5R,2'R,5'R,2''R)-1-(dodecahydro-[2,2';5',2'']terfuran-5-yl)-pent-4-enyloxy]-diphenyl-silane (444884-33-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 50 ℃; for 3h;

DOI:10.1016/S0040-4020(02)00075-3

Reference yield:

3-((4R,5R)-5-{(R)-3-[(2R,5R)-5-((R)-2,2-Dimethyl-[1,3]dioxepan-4-yl)-tetrahydro-furan-2-yl]-3-iodo-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionaldehyde (444884-35-9) → tert-Butyl-[(R)-(2S,5R,2'R,5'R,2''R)-1-(dodecahydro-[2,2';5',2'']terfuran-5-yl)-pent-4-enyloxy]-diphenyl-silane (444884-33-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium bis(trimethylsilyl) amide / toluene / 1 h / 20 °C

1.2: 86 percent / toluene / -78 - 20 °C

2.1: 70 percent / PPTS / ethanol / 3 h

3.1: 85 percent / Ph₃P; DEAD / CH₂Cl₂ / 2 h

4.1: 93 percent Turnov_. / BF₃*Et₂O / tetrahydrofuran; H₂O / 48 h / 20 °C

5.1: 96 percent / Bu₂SnO / benzene / 17 h / Heating

6.1: 66 percent / imidazole / dimethylformamide / 3 h / 50 °C

With 1H-imidazole; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; di(n-butyl)tin oxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 1.2: Wittig reaction / 3.1: Mitsunobu etherification;

DOI:10.1016/S0040-4020(02)00075-3

Reference yield:

3-((4R,5R)-5-{(R)-3-[(2R,5R)-5-((R)-2,2-Dimethyl-[1,3]dioxepan-4-yl)-tetrahydro-furan-2-yl]-3-iodo-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-ol (221367-57-3) → tert-Butyl-[(R)-(2S,5R,2'R,5'R,2''R)-1-(dodecahydro-[2,2';5',2'']terfuran-5-yl)-pent-4-enyloxy]-diphenyl-silane (444884-33-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 90 percent / oxalyl chloride; DMSO / CH₂Cl₂ / 0.42 h / -78 °C

2.1: sodium bis(trimethylsilyl) amide / toluene / 1 h / 20 °C

2.2: 86 percent / toluene / -78 - 20 °C

3.1: 70 percent / PPTS / ethanol / 3 h

4.1: 85 percent / Ph₃P; DEAD / CH₂Cl₂ / 2 h

5.1: 93 percent Turnov_. / BF₃*Et₂O / tetrahydrofuran; H₂O / 48 h / 20 °C

6.1: 96 percent / Bu₂SnO / benzene / 17 h / Heating

7.1: 66 percent / imidazole / dimethylformamide / 3 h / 50 °C

With 1H-imidazole; oxalyl dichloride; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; di(n-butyl)tin oxide; dimethyl sulfoxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 1.1: Swern oxidation / 2.2: Wittig reaction / 4.1: Mitsunobu etherification;

DOI:10.1016/S0040-4020(02)00075-3

upstream raw materials:

tert-butylchlorodiphenylsilane

(R)-(2S,5R,2'R,5'R,2''R)-1-(Dodecahydro-[2,2';5',2'']terfuran-5-yl)-pent-4-en-1-ol

3-((4R,5R)-5-{(R)-3-[(2R,5R)-5-((R)-2,2-Dimethyl-[1,3]dioxepan-4-yl)-tetrahydro-furan-2-yl]-3-iodo-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionaldehyde

3-((4R,5R)-5-{(R)-3-[(2R,5R)-5-((R)-2,2-Dimethyl-[1,3]dioxepan-4-yl)-tetrahydro-furan-2-yl]-3-iodo-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-ol

Downstream raw materials:

(R)-4-(tert-Butyl-diphenyl-silanyloxy)-4-(2S,5R,2'R,5'R,2''R)-dodecahydro-[2,2';5',2'']terfuran-5-yl-butyric acid

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