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

Base Information

• Chemical Name: 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
• CAS No.: 916197-47-2
• Molecular Formula: C₃₉H₄₈O₈Si
• Molecular Weight: 672.891

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 6 articles about 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 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: 79.0%

5-methoxy-3,3-dimethyl-1,5-cyclohexadien-1-yl acetate (916197-46-1) + (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) → 4-((5S)-5-{[tert-butyl(diphenyl)silyl]oxy}hexanoyl)-3-methoxy-5-(2,4,10-trioxatricyclo[3.3.1.13,7]dec-3-ylmethyl)phenyl acetate (916197-47-2)

Guidance literature:

at 180 ℃; for 72h;

DOI:10.1021/ja064270e

Reference yield:

ethyl (E,5S)-5-{[tert-butyl(diphenyl)silyl]oxy}-2-hexenoate (378749-99-6) → 4-((5S)-5-{[tert-butyl(diphenyl)silyl]oxy}hexanoyl)-3-methoxy-5-(2,4,10-trioxatricyclo[3.3.1.13,7]dec-3-ylmethyl)phenyl acetate (916197-47-2)

Guidance literature:

Multi-step reaction with 4 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

4.1: 79 percent / 72 h / 180 °C

With n-butyllithium; hydrogen; isopropylmagnesium chloride; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; Petroleum ether; 4.1: Diels-Alder reaction;

DOI:10.1021/ja064270e

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 4-((5S)-5-{[tert-butyl(diphenyl)silyl]oxy}hexanoyl)-3-methoxy-5-(2,4,10-trioxatricyclo[3.3.1.13,7]dec-3-ylmethyl)phenyl acetate (916197-47-2)

Guidance literature:

Multi-step reaction with 7 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

7.1: 79 percent / 72 h / 180 °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; 7.1: Diels-Alder reaction;

DOI:10.1021/ja064270e

upstream raw materials:

5-methoxy-3,3-dimethyl-1,5-cyclohexadien-1-yl acetate

(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

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

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

Downstream raw materials:

methyl 2-{5-hydroxy-2-[(5S)-5-hydroxyhexanoyl]-3-methoxyphenyl}acetate

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