(8R,9S,10R,11R,12S)-15-chloro-14-(4-ethoxybenzyl)-2,3,4,5,7,8,9,10,11,12-decahydro-2H-8,12-epoxybenzo[g][1,6]-dioxacyclotetradecine-9,10,11-triol

Base Information

Chemical Name:(8R,9S,10R,11R,12S)-15-chloro-14-(4-ethoxybenzyl)-2,3,4,5,7,8,9,10,11,12-decahydro-2H-8,12-epoxybenzo[g][1,6]-dioxacyclotetradecine-9,10,11-triol
CAS No.:1338728-33-8
Molecular Formula:C₂₅H₃₁ClO₇
Molecular Weight:478.97
Hs Code.:

Synonyms:(8R,9S,10R,11R,12S)-15-chloro-14-(4-ethoxybenzyl)-2,3,4,5,7,8,9,10,11,12-decahydro-2H-8,12-epoxybenzo[g][1,6]-dioxacyclotetradecine-9,10,11-triol

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Chemical Property of (8R,9S,10R,11R,12S)-15-chloro-14-(4-ethoxybenzyl)-2,3,4,5,7,8,9,10,11,12-decahydro-2H-8,12-epoxybenzo[g][1,6]-dioxacyclotetradecine-9,10,11-triol

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Technology Process of (8R,9S,10R,11R,12S)-15-chloro-14-(4-ethoxybenzyl)-2,3,4,5,7,8,9,10,11,12-decahydro-2H-8,12-epoxybenzo[g][1,6]-dioxacyclotetradecine-9,10,11-triol

There total 19 articles about (8R,9S,10R,11R,12S)-15-chloro-14-(4-ethoxybenzyl)-2,3,4,5,7,8,9,10,11,12-decahydro-2H-8,12-epoxybenzo[g][1,6]-dioxacyclotetradecine-9,10,11-triol 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: 22.0%

: 1338728-32-7
(Z)-(8R,9R,10R,11S,12S)-9,10,11-tris(benzyloxy)-15-chloro-14-(4-ethoxybenzyl)-5,7,8,9,10,11,12-heptahydro-2H-8,12-epoxybenzo[g][1,6]dioxacyclotetradecine

: 1338728-33-8
(8R,9S,10R,11R,12S)-15-chloro-14-(4-ethoxybenzyl)-2,3,4,5,7,8,9,10,11,12-decahydro-2H-8,12-epoxybenzo[g][1,6]-dioxacyclotetradecine-9,10,11-triol

Guidance literature:: With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20 ℃;
DOI:10.1016/j.bmc.2011.07.045

Reference yield:

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

: 1338728-33-8
(8R,9S,10R,11R,12S)-15-chloro-14-(4-ethoxybenzyl)-2,3,4,5,7,8,9,10,11,12-decahydro-2H-8,12-epoxybenzo[g][1,6]-dioxacyclotetradecine-9,10,11-triol

Guidance literature:: Multi-step reaction with 17 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: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

12.2: 5 h / 0 - 20 °C / Inert atmosphere

13.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1.5 h / -55 - -45 °C / Inert atmosphere

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

14.2: 0 °C / Inert atmosphere

15.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

15.2: 5 h / 0 - 20 °C / Inert atmosphere

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

17.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 20 °C

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; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; water; hydrogen; sodium methylate; sodium hydride; potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide; sodium thioethylate; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil;
DOI:10.1016/j.bmc.2011.07.045

Reference yield:

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

: 1338728-33-8
(8R,9S,10R,11R,12S)-15-chloro-14-(4-ethoxybenzyl)-2,3,4,5,7,8,9,10,11,12-decahydro-2H-8,12-epoxybenzo[g][1,6]-dioxacyclotetradecine-9,10,11-triol

Guidance literature:: Multi-step reaction with 18 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: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

13.2: 5 h / 0 - 20 °C / Inert atmosphere

14.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1.5 h / -55 - -45 °C / Inert atmosphere

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

15.2: 0 °C / Inert atmosphere

16.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

16.2: 5 h / 0 - 20 °C / Inert atmosphere

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

18.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 20 °C

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; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; water; hydrogen; sodium methylate; sodium hydride; potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide; sodium thioethylate; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil;
DOI:10.1016/j.bmc.2011.07.045