(3R,4R,5S,6R )-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Base Information

Chemical Name:(3R,4R,5S,6R )-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
CAS No.:1338728-14-5
Molecular Formula:C₂₄H₂₉ClO₇
Molecular Weight:464.943
Hs Code.:

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

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

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

There total 11 articles about (3R,4R,5S,6R )-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-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:

: 1338728-13-4
(3R,4S,5S,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

: 1338728-14-5
(3R,4R,5S,6R )-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; acetonitrile; at -25 - 0 ℃; for 3h; Inert atmosphere;
DOI:10.1016/j.bmc.2011.07.045

Reference yield:

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

: 1338728-14-5
(3R,4R,5S,6R )-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 10 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

With triethylsilane; aluminum (III) chloride; n-butyllithium; thionyl chloride; methanesulfonic acid; lithium hydroxide monohydrate; boron trifluoride diethyl etherate; water; potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide; sodium thioethylate; In tetrahydrofuran; 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

: 1338728-14-5
(3R,4R,5S,6R )-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 9 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

With triethylsilane; aluminum (III) chloride; n-butyllithium; thionyl chloride; methanesulfonic acid; boron trifluoride diethyl etherate; water; potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide; sodium thioethylate; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/j.bmc.2011.07.045