[2-(2-benzyloxy-ethyl)-8-bromo-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-yloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [2-(2-benzyloxy-ethyl)-8-bromo-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-yloxy]-tert-butyl-dimethyl-silane
• CAS No.: 926653-34-1
• Molecular Formula: C₂₅H₄₁BrO₃Si
• Molecular Weight: 497.588

Synonyms:[2-(2-benzyloxy-ethyl)-8-bromo-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-yloxy]-tert-butyl-dimethyl-silane

Chemical Property of [2-(2-benzyloxy-ethyl)-8-bromo-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-yloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2-(2-benzyloxy-ethyl)-8-bromo-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-yloxy]-tert-butyl-dimethyl-silane

There total 28 articles about [2-(2-benzyloxy-ethyl)-8-bromo-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-yloxy]-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: 67.0%

9-(2-benzyloxy-ethyl)-8-(tert-butyl-dimethyl-silanyloxy)-2-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-ol → [2-(2-benzyloxy-ethyl)-8-bromo-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-yloxy]-tert-butyl-dimethyl-silane (926653-34-1)

Guidance literature:

With pyridine; carbon tetrabromide; TOP; 1-methylcyclohex-1-ene; In toluene; at 80 ℃;

DOI:10.1016/j.tetlet.2006.11.080

Reference yield:

4-[1-(4-methoxy-benzyloxy)-pent-4-ynyl]-2,2-dimethyl-[1,3]dioxolane (926653-19-2) → [2-(2-benzyloxy-ethyl)-8-bromo-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-yloxy]-tert-butyl-dimethyl-silane (926653-34-1)

Guidance literature:

Multi-step reaction with 28 steps

1.1: 81 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

2.1: 88 percent / TEA; DMAP / CH₂Cl₂ / 0 °C

3.1: TBAF / tetrahydrofuran

3.2: 91 percent / K₂CO₃ / methanol

4.1: 89 percent / aq. AcOH

5.1: 99 percent / H₂; quinoline / Lindlar catalyst / ethyl acetate

6.1: 97 percent / TEA; DMAP / CH₂Cl₂

7.1: Eu(fod)3 / toluene / 120 °C

7.2: 70 percent / AcOH; H₂O / tetrahydrofuran

8.1: 95 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂ / 0 °C

9.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

10.1: 58 percent / CF₃CO₂H / methanol

11.1: 99 percent / PPTS / CH₂Cl₂

12.1: 98 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 0 °C

13.1: (PhSe)2; NaBH₄ / ethanol; butan-1-ol / Heating

13.2: H₂O₂; pyridine; 2-methyl-2-butene / CH₂Cl₂

14.1: 85 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 0 °C

15.1: 92 percent / TEA; DMAP / CH₂Cl₂ / 0 °C

16.1: (PhSe)2; NaBH₄ / ethanol; butan-1-ol / 80 °C

16.2: H₂O₂; pyridine; 2-nethyl-2-butene / CH₂Cl₂

17.1: 75 percent / DIBAL; n-BuLi / toluene / 0 °C

18.1: 100 percent / TBAF / tetrahydrofuran

19.1: 97 percent / imidazole / dimethylformamide

20.1: 97 percent / CBr₄; P(oct)3; TEA / 1-methyl-1-cyclohexene / toluene / 90 °C

21.1: 100 percent / Bu₃SnH; AIBN / toluene / 0 °C / Irradiation

22.1: 78 percent / CSA; (HOCH₂)2 / methanol

23.1: 100 percent / CSA / 1,2-dichloro-ethane

24.1: 97 percent / DIBAL / toluene / -10 °C

25.1: TEA; DMAP / CH₂Cl₂

26.1: CuI / diethyl ether / -12 °C

27.1: 91 percent / DDQ / benzene / pH 7.4

28.1: 67 percent / CBr₄; P(oct)3; pyridine / 1-methyl-1-cyclohexene / toluene / 80 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; quinoline; dmap; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; TOP; 4 A molecular sieve; TEA; diphenyl diselenide; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; ethylene glycol; acetic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Eu(fod)3; Lindlar's catalyst; 1-methylcyclohex-1-ene; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; butan-1-ol; benzene; 1.1: Yamaguchi reaction;

DOI:10.1016/j.tetlet.2006.11.080

Reference yield:

9-[2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-2,3,4,5,8,9-hexahydro-oxonine-2-carbaldehyde → [2-(2-benzyloxy-ethyl)-8-bromo-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-yloxy]-tert-butyl-dimethyl-silane (926653-34-1)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 99 percent / PPTS / CH₂Cl₂

2.1: 98 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 0 °C

3.1: (PhSe)2; NaBH₄ / ethanol; butan-1-ol / Heating

3.2: H₂O₂; pyridine; 2-methyl-2-butene / CH₂Cl₂

4.1: 85 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 0 °C

5.1: 92 percent / TEA; DMAP / CH₂Cl₂ / 0 °C

6.1: (PhSe)2; NaBH₄ / ethanol; butan-1-ol / 80 °C

6.2: H₂O₂; pyridine; 2-nethyl-2-butene / CH₂Cl₂

7.1: 75 percent / DIBAL; n-BuLi / toluene / 0 °C

8.1: 100 percent / TBAF / tetrahydrofuran

9.1: 97 percent / imidazole / dimethylformamide

10.1: 97 percent / CBr₄; P(oct)3; TEA / 1-methyl-1-cyclohexene / toluene / 90 °C

11.1: 100 percent / Bu₃SnH; AIBN / toluene / 0 °C / Irradiation

12.1: 78 percent / CSA; (HOCH₂)2 / methanol

13.1: 100 percent / CSA / 1,2-dichloro-ethane

14.1: 97 percent / DIBAL / toluene / -10 °C

15.1: TEA; DMAP / CH₂Cl₂

16.1: CuI / diethyl ether / -12 °C

17.1: 91 percent / DDQ / benzene / pH 7.4

18.1: 67 percent / CBr₄; P(oct)3; pyridine / 1-methyl-1-cyclohexene / toluene / 80 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; TOP; TEA; diphenyl diselenide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; ethylene glycol; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 1-methylcyclohex-1-ene; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; butan-1-ol; benzene;

DOI:10.1016/j.tetlet.2006.11.080

upstream raw materials:

4-[1-(4-methoxy-benzyloxy)-pent-4-ynyl]-2,2-dimethyl-[1,3]dioxolane

6-(2-benzyloxy-1-hydroxy-ethyl)-2,2-dimethyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-ol

9-(2-benzyloxy-ethyl)-8-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-2,3,4,7,8,9-hexahydro-oxonin-3-ol

[6-(2-benzyloxy-ethyl)-2,2-dimethyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-yloxy]-tert-butyl-dimethyl-silane

Downstream raw materials:

(+)-obtusenyne

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