(2R,4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9,10a-Dimethyl-2-phenyl-8-vinyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ol

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Chemical Name:(2R,4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9,10a-Dimethyl-2-phenyl-8-vinyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ol
CAS No.:494760-40-6
Molecular Formula:C₂₄H₃₂O₆
Molecular Weight:416.514
Hs Code.:

Synonyms:(2R,4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9,10a-Dimethyl-2-phenyl-8-vinyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ol

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Chemical Property of (2R,4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9,10a-Dimethyl-2-phenyl-8-vinyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ol

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Technology Process of (2R,4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9,10a-Dimethyl-2-phenyl-8-vinyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ol

There total 14 articles about (2R,4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9,10a-Dimethyl-2-phenyl-8-vinyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-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%

: 494760-73-5
tert-Butyl-((2R,4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9,10a-dimethyl-2-phenyl-8-vinyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-yloxy)-dimethyl-silane

: 494760-40-6
(2R,4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9,10a-Dimethyl-2-phenyl-8-vinyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 14h; Heating;
DOI:10.1021/ja036984k

Reference yield:

: 361534-79-4
((2R,4aR,6R,7S,8aR,9aS,10aS)-6-Hydroxy-6,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-acetic acid ethyl ester

: 494760-40-6
(2R,4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9,10a-Dimethyl-2-phenyl-8-vinyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ol

Guidance literature:: Multi-step reaction with 13 steps

1.1: LiAlH₄ / diethyl ether / 1 h / 0 °C

2.1: 1.56 g / 2,6-lutidine / CH₂Cl₂ / 2 h / Heating

3.1: 100 percent / H₂ / Pd(OH)2-C / ethyl acetate / 49 h

4.1: 599 mg / Et₃N / CH₂Cl₂ / 3 h / Heating

5.1: 95 percent / CuBr / tetrahydrofuran; diethyl ether / 1 h / -20 - 20 °C

6.1: O₃(g) / methanol; CH₂Cl₂ / -78 °C

6.2: Me₂S; NaBH₄ / methanol; CH₂Cl₂ / 1 h / 0 °C

7.1: 2.13 g / pyridine / CH₂Cl₂ / 20 °C

8.1: O₃(g) / methanol; CH₂Cl₂ / -78 °C

8.2: NaBH₄ / methanol; CH₂Cl₂ / 1 h / 20 °C

9.1: CSA / CH₂Cl₂ / 1 h / 0 °C

10.1: 2.03 g / aq. AcOH / tetrahydrofuran / 3 h / 30 °C

11.1: 2-nitrophenyl selenocyanate; Bu₃P / tetrahydrofuran / 0.5 h / 20 °C

11.2: 97 percent / NaHCO₃; aq. H₂O₂ / tetrahydrofuran / 1 h / 40 °C

12.1: 100 percent / TBAF / tetrahydrofuran / 14 h / Heating

With pyridine; 2,6-dimethylpyridine; lithium aluminium tetrahydride; ortho-nitrophenyl selenocyanate; tributylphosphine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; ozone; acetic acid; triethylamine; copper(I) bromide; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1021/ja036984k

Reference yield:

: (2R,4aR,6R,7S,8aR,9aS,10aS)-7-(2-Hydroxy-ethyl)-6,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-ol

: 494760-40-6
(2R,4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9,10a-Dimethyl-2-phenyl-8-vinyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 1.56 g / 2,6-lutidine / CH₂Cl₂ / 2 h / Heating

2.1: 100 percent / H₂ / Pd(OH)2-C / ethyl acetate / 49 h

3.1: 599 mg / Et₃N / CH₂Cl₂ / 3 h / Heating

4.1: 95 percent / CuBr / tetrahydrofuran; diethyl ether / 1 h / -20 - 20 °C

5.1: O₃(g) / methanol; CH₂Cl₂ / -78 °C

5.2: Me₂S; NaBH₄ / methanol; CH₂Cl₂ / 1 h / 0 °C

6.1: 2.13 g / pyridine / CH₂Cl₂ / 20 °C

7.1: O₃(g) / methanol; CH₂Cl₂ / -78 °C

7.2: NaBH₄ / methanol; CH₂Cl₂ / 1 h / 20 °C

8.1: CSA / CH₂Cl₂ / 1 h / 0 °C

9.1: 2.03 g / aq. AcOH / tetrahydrofuran / 3 h / 30 °C

10.1: 2-nitrophenyl selenocyanate; Bu₃P / tetrahydrofuran / 0.5 h / 20 °C

10.2: 97 percent / NaHCO₃; aq. H₂O₂ / tetrahydrofuran / 1 h / 40 °C

11.1: 100 percent / TBAF / tetrahydrofuran / 14 h / Heating

With pyridine; 2,6-dimethylpyridine; ortho-nitrophenyl selenocyanate; tributylphosphine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; ozone; acetic acid; triethylamine; copper(I) bromide; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1021/ja036984k