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

Base Information

• Chemical Name: (2S,3S,4R,5R,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(allyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 1338728-28-1
• Molecular Formula: C₃₃H₃₉ClO₁₀
• Molecular Weight: 631.12

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

Chemical Property of (2S,3S,4R,5R,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(allyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (2S,3S,4R,5R,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(allyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 15 articles about (2S,3S,4R,5R,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(allyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 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:

5-bromo-2-chloro-4-hydroxybenzonitrile (1259020-46-6) → (2S,3S,4R,5R,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(allyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1338728-28-1)

Guidance literature:

Multi-step reaction with 15 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

With pyridine; 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:

5-bromo-2-chloro-4-methoxybenzonitrile (1259020-79-5) → (2S,3S,4R,5R,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(allyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1338728-28-1)

Guidance literature:

Multi-step reaction with 14 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

With pyridine; 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

Reference yield:

5-bromo-2-chloro-4-methoxybenzoic acid (1259020-48-8) → (2S,3S,4R,5R,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(allyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1338728-28-1)

Guidance literature:

Multi-step reaction with 13 steps

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

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

2.2: 20 °C / Inert atmosphere

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

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

4.2: 0 °C / Inert atmosphere

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

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

6.2: 1.5 h / -78 °C / Inert atmosphere

6.3: -78 °C / Inert atmosphere

7.1: methanesulfonic acid / 20 °C / Inert atmosphere

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

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

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

10.2: 0 °C / Inert atmosphere

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

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

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

With pyridine; triethylsilane; dmap; aluminum (III) chloride; n-butyllithium; thionyl chloride; methanesulfonic acid; trifluorormethanesulfonic acid; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; sodium cyanoborohydride; potassium carbonate; N,N-dimethyl-formamide; sodium thioethylate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1016/j.bmc.2011.07.045

upstream raw materials:

5-bromo-2-chloro-4-hydroxybenzonitrile

5-bromo-2-chloro-4-methoxybenzonitrile

5-bromo-2-chloro-4-methoxybenzoic acid

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

(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

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

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