(8S)-8-{[tert-butyl(diphenyl)silyl]oxy}-1-(2,4,10-trioxatricyclo[3.3.1.1^3,7]dec-3-yl)-2-nonyn-4-one

Base Information

• Chemical Name: (8S)-8-{[tert-butyl(diphenyl)silyl]oxy}-1-(2,4,10-trioxatricyclo[3.3.1.1^3,7]dec-3-yl)-2-nonyn-4-one
• CAS No.: 916197-45-0
• Molecular Formula: C₃₂H₄₀O₅Si
• Molecular Weight: 532.752

Synonyms:(8S)-8-{[tert-butyl(diphenyl)silyl]oxy}-1-(2,4,10-trioxatricyclo[3.3.1.1^3,7]dec-3-yl)-2-nonyn-4-one

Chemical Property of (8S)-8-{[tert-butyl(diphenyl)silyl]oxy}-1-(2,4,10-trioxatricyclo[3.3.1.1^3,7]dec-3-yl)-2-nonyn-4-one

Chemical Property:

Purity/Quality:

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Technology Process of (8S)-8-{[tert-butyl(diphenyl)silyl]oxy}-1-(2,4,10-trioxatricyclo[3.3.1.1^3,7]dec-3-yl)-2-nonyn-4-one

There total 7 articles about (8S)-8-{[tert-butyl(diphenyl)silyl]oxy}-1-(2,4,10-trioxatricyclo[3.3.1.1^3,7]dec-3-yl)-2-nonyn-4-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: 84.0%

3-(3,3-dibromo-2-propenyl)-2,4,10-trioxatricyclo[3.3.1.13,7]decanediene (916197-42-7) + (5S)-5-{[tert-butyl(diphenyl)silyl]oxy}-N-methoxy-N-methylhexanamide (916197-44-9) → (8S)-8-{[tert-butyl(diphenyl)silyl]oxy}-1-(2,4,10-trioxatricyclo[3.3.1.13,7]dec-3-yl)-2-nonyn-4-one (916197-45-0)

Guidance literature:

3-(3,3-dibromo-2-propenyl)-2,4,10-trioxatricyclo[3.3.1.1^3,7]decanediene; With n-butyllithium; In tetrahydrofuran; Petroleum ether; at 0 ℃; for 0.5h;

(5S)-5-{[tert-butyl(diphenyl)silyl]oxy}-N-methoxy-N-methylhexanamide; In tetrahydrofuran; Petroleum ether; at -78 - 20 ℃; for 3h; Further stages.;

DOI:10.1021/ja064270e

Reference yield:

ethyl (E,5S)-5-{[tert-butyl(diphenyl)silyl]oxy}-2-hexenoate (378749-99-6) → (8S)-8-{[tert-butyl(diphenyl)silyl]oxy}-1-(2,4,10-trioxatricyclo[3.3.1.13,7]dec-3-yl)-2-nonyn-4-one (916197-45-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / H₂ / Pd/C / ethyl acetate / 2.5 h / 20 °C

2.1: 96 percent / isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / -20 °C

3.1: n-butyllithium / petroleum ether; tetrahydrofuran / 0.5 h / 0 °C

3.2: 84 percent / petroleum ether; tetrahydrofuran / 3 h / -78 - 20 °C

With n-butyllithium; hydrogen; isopropylmagnesium chloride; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; Petroleum ether;

DOI:10.1021/ja064270e

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (8S)-8-{[tert-butyl(diphenyl)silyl]oxy}-1-(2,4,10-trioxatricyclo[3.3.1.13,7]dec-3-yl)-2-nonyn-4-one (916197-45-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 99 percent / imidazole / dimethylformamide / 0 - 20 °C

2.1: 94 percent / diisobutylaluminium hydride / hexane; CH₂Cl₂ / 0.25 h / -78 °C

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.33 h / 20 °C

3.2: 90 percent / acetonitrile

4.1: 100 percent / H₂ / Pd/C / ethyl acetate / 2.5 h / 20 °C

5.1: 96 percent / isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / -20 °C

6.1: n-butyllithium / petroleum ether; tetrahydrofuran / 0.5 h / 0 °C

6.2: 84 percent / petroleum ether; tetrahydrofuran / 3 h / -78 - 20 °C

With 1H-imidazole; n-butyllithium; hydrogen; isopropylmagnesium chloride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; Petroleum ether;

DOI:10.1021/ja064270e

upstream raw materials:

3-(3,3-dibromo-2-propenyl)-2,4,10-trioxatricyclo[3.3.1.1^3,7]decanediene

(5S)-5-{[tert-butyl(diphenyl)silyl]oxy}-N-methoxy-N-methylhexanamide

ethyl (5S)-5-{[tert-butyl(diphenyl)silyl]oxy}hexanoate

2-(2,4,10-Trioxatricyclo<3.3.1.1^3,7>dec-3-yl)ethanal

Downstream raw materials:

4-((5S)-5-{[tert-butyl(diphenyl)silyl]oxy}hexanoyl)-3-methoxy-5-(2,4,10-trioxatricyclo[3.3.1.1^3,7]dec-3-ylmethyl)phenyl acetate

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