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

Base Information

Chemical Name:6-(2-benzyloxy-1-hydroxy-ethyl)-2,2-dimethyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-ol
CAS No.:926653-41-0
Molecular Formula:C₂₁H₃₀O₆
Molecular Weight:378.466
Hs Code.:

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

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

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

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

There total 19 articles about 6-(2-benzyloxy-1-hydroxy-ethyl)-2,2-dimethyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-ol 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: 100.0%

: 926653-28-3
6-[2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-ol

: 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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
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

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

Guidance literature:: Multi-step reaction with 18 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

With 2,6-dimethylpyridine; quinoline; dmap; sodium tetrahydroborate; n-butyllithium; 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; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; toluene; butan-1-ol; 1.1: Yamaguchi reaction;
DOI:10.1016/j.tetlet.2006.11.080

Reference yield:

: 926653-20-5
4-[6-(3-benzyloxymethyl-oxiranyl)-1-(4-methoxy-benzyloxy)-hex-4-ynyl]-2,2-dimethyl-[1,3]dioxolane

: 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

Guidance literature:: Multi-step reaction with 15 steps

1.1: 89 percent / aq. AcOH

2.1: 99 percent / H₂; quinoline / Lindlar catalyst / ethyl acetate

3.1: 97 percent / TEA; DMAP / CH₂Cl₂

4.1: Eu(fod)3 / toluene / 120 °C

4.2: 70 percent / AcOH; H₂O / tetrahydrofuran

5.1: 95 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂ / 0 °C

6.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

7.1: 58 percent / CF₃CO₂H / methanol

8.1: 99 percent / PPTS / CH₂Cl₂

9.1: 98 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 0 °C

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

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

11.1: 85 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 0 °C

12.1: 92 percent / TEA; DMAP / CH₂Cl₂ / 0 °C

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

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

14.1: 75 percent / DIBAL; n-BuLi / toluene / 0 °C

15.1: 100 percent / TBAF / tetrahydrofuran

With 2,6-dimethylpyridine; quinoline; dmap; sodium tetrahydroborate; n-butyllithium; 4 A molecular sieve; TEA; diphenyl diselenide; 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; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; toluene; butan-1-ol;
DOI:10.1016/j.tetlet.2006.11.080