(8R,9R,10R,11S,12S)-9,10,11-tris(acetyloxy)-15-chloro-14-(4-ethoxybenzyl)-5,7,8,9,10,11,12-heptahydro-2H-8,12-epoxybenzo[g][1,6]dioxacyclotetradecine

Base Information

Chemical Name:(8R,9R,10R,11S,12S)-9,10,11-tris(acetyloxy)-15-chloro-14-(4-ethoxybenzyl)-5,7,8,9,10,11,12-heptahydro-2H-8,12-epoxybenzo[g][1,6]dioxacyclotetradecine
CAS No.:1338728-29-2
Molecular Formula:C₃₁H₃₅ClO₁₀
Molecular Weight:603.066
Hs Code.:

(8R,9R,10R,11S,12S)-9,10,11-tris(acetyloxy)-15-chloro-14-(4-ethoxybenzyl)-5,7,8,9,10,11,12-heptahydro-2H-8,12-epoxybenzo[g][1,6]dioxacyclotetradecine

Synonyms:(8R,9R,10R,11S,12S)-9,10,11-tris(acetyloxy)-15-chloro-14-(4-ethoxybenzyl)-5,7,8,9,10,11,12-heptahydro-2H-8,12-epoxybenzo[g][1,6]dioxacyclotetradecine

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Chemical Property of (8R,9R,10R,11S,12S)-9,10,11-tris(acetyloxy)-15-chloro-14-(4-ethoxybenzyl)-5,7,8,9,10,11,12-heptahydro-2H-8,12-epoxybenzo[g][1,6]dioxacyclotetradecine

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Technology Process of (8R,9R,10R,11S,12S)-9,10,11-tris(acetyloxy)-15-chloro-14-(4-ethoxybenzyl)-5,7,8,9,10,11,12-heptahydro-2H-8,12-epoxybenzo[g][1,6]dioxacyclotetradecine

There total 17 articles about (8R,9R,10R,11S,12S)-9,10,11-tris(acetyloxy)-15-chloro-14-(4-ethoxybenzyl)-5,7,8,9,10,11,12-heptahydro-2H-8,12-epoxybenzo[g][1,6]dioxacyclotetradecine 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: 23.0%

: 1338728-28-1
(2S,3S,4R,5R,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(allyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 1338728-29-2
(8R,9R,10R,11S,12S)-9,10,11-tris(acetyloxy)-15-chloro-14-(4-ethoxybenzyl)-5,7,8,9,10,11,12-heptahydro-2H-8,12-epoxybenzo[g][1,6]dioxacyclotetradecine

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 60 ℃; for 72h; Inert atmosphere;
DOI:10.1016/j.bmc.2011.07.045

Reference yield:

: 1259020-46-6
5-bromo-2-chloro-4-hydroxybenzonitrile

: 1338728-29-2
(8R,9R,10R,11S,12S)-9,10,11-tris(acetyloxy)-15-chloro-14-(4-ethoxybenzyl)-5,7,8,9,10,11,12-heptahydro-2H-8,12-epoxybenzo[g][1,6]dioxacyclotetradecine

Guidance literature:: Multi-step reaction with 16 steps

1.1: lithium hydroxide monohydrate / tetrahydrofuran / 5 h / 75 °C / Inert atmosphere

2.1: water; sodium hydroxide / ethanol / 100 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

3.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 4 h / 90 °C / Inert atmosphere

4.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 2 h / -10 - 0 °C / Inert atmosphere

6.1: sodium thioethylate / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere

6.2: 0 °C / Inert atmosphere

7.1: potassium carbonate / acetone / 3 h / 65 °C / Inert atmosphere

8.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 1 h / -78 °C / Inert atmosphere

8.2: 1.5 h / -78 °C / Inert atmosphere

8.3: -78 °C / Inert atmosphere

9.1: methanesulfonic acid / 20 °C / Inert atmosphere

10.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 3 h / -25 - 0 °C / Inert atmosphere

11.1: pyridine; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

12.1: sodium methylate / methanol / 5 h / 20 °C / Inert atmosphere

12.2: 0 °C / Inert atmosphere

13.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

14.1: trifluorormethanesulfonic acid; sodium cyanoborohydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

15.1: pyridine; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

16.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 72 h / 60 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; triethylsilane; dmap; aluminum (III) chloride; n-butyllithium; thionyl chloride; methanesulfonic acid; lithium hydroxide monohydrate; trifluorormethanesulfonic acid; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; water; sodium methylate; sodium cyanoborohydride; potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide; sodium thioethylate; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/j.bmc.2011.07.045

Reference yield:

: 1259020-79-5
5-bromo-2-chloro-4-methoxybenzonitrile

: 1338728-29-2
(8R,9R,10R,11S,12S)-9,10,11-tris(acetyloxy)-15-chloro-14-(4-ethoxybenzyl)-5,7,8,9,10,11,12-heptahydro-2H-8,12-epoxybenzo[g][1,6]dioxacyclotetradecine

Guidance literature:: Multi-step reaction with 15 steps

1.1: water; sodium hydroxide / ethanol / 100 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 4 h / 90 °C / Inert atmosphere

3.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 2 h / -10 - 0 °C / Inert atmosphere

5.1: sodium thioethylate / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere

5.2: 0 °C / Inert atmosphere

6.1: potassium carbonate / acetone / 3 h / 65 °C / Inert atmosphere

7.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 1 h / -78 °C / Inert atmosphere

7.2: 1.5 h / -78 °C / Inert atmosphere

7.3: -78 °C / Inert atmosphere

8.1: methanesulfonic acid / 20 °C / Inert atmosphere

9.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 3 h / -25 - 0 °C / Inert atmosphere

10.1: pyridine; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

11.1: sodium methylate / methanol / 5 h / 20 °C / Inert atmosphere

11.2: 0 °C / Inert atmosphere

12.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

13.1: trifluorormethanesulfonic acid; sodium cyanoborohydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

14.1: pyridine; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

15.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 72 h / 60 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; triethylsilane; dmap; aluminum (III) chloride; n-butyllithium; thionyl chloride; methanesulfonic acid; trifluorormethanesulfonic acid; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; water; sodium methylate; sodium cyanoborohydride; potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide; sodium thioethylate; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/j.bmc.2011.07.045