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

Base Information

Chemical Name:[6-(2-benzyloxy-1-bromo-ethyl)-2,2-dimethyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-yloxy]-tert-butyl-dimethyl-silane
CAS No.:926653-30-7
Molecular Formula:C₂₇H₄₃BrO₅Si
Molecular Weight:555.625
Hs Code.:

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

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

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

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

There total 20 articles about [6-(2-benzyloxy-1-bromo-ethyl)-2,2-dimethyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-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: 97.0%

: 926653-29-4
2-benzyloxy-1-[7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-6-yl]-ethanol

: 926653-30-7
[6-(2-benzyloxy-1-bromo-ethyl)-2,2-dimethyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: With carbon tetrabromide; TOP; TEA; 1-methylcyclohex-1-ene; In toluene; at 90 ℃;
DOI:10.1016/j.tetlet.2006.11.080

Reference yield:

: 926653-19-2
4-[1-(4-methoxy-benzyloxy)-pent-4-ynyl]-2,2-dimethyl-[1,3]dioxolane

: 926653-30-7
[6-(2-benzyloxy-1-bromo-ethyl)-2,2-dimethyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 20 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

With 1H-imidazole; 2,6-dimethylpyridine; quinoline; dmap; sodium tetrahydroborate; n-butyllithium; carbon tetrabromide; TOP; 4 A molecular sieve; TEA; diphenyl diselenide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; 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; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; butan-1-ol; 1.1: Yamaguchi reaction;
DOI:10.1016/j.tetlet.2006.11.080

Reference yield:

: 926653-41-0
6-(2-benzyloxy-1-hydroxy-ethyl)-2,2-dimethyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-ol

: 926653-30-7
[6-(2-benzyloxy-1-bromo-ethyl)-2,2-dimethyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 2 steps

1: 97 percent / imidazole / dimethylformamide

2: 97 percent / CBr₄; P(oct)3; TEA / 1-methyl-1-cyclohexene / toluene / 90 °C

With 1H-imidazole; carbon tetrabromide; TOP; TEA; 1-methylcyclohex-1-ene; In N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tetlet.2006.11.080