(2S,3R,4R,5S,6R)-2-(6-(4-ethylbenzyl)-7-chloro-2,3-dihydrobenzofuran-4-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4R,5S,6R)-2-(6-(4-ethylbenzyl)-7-chloro-2,3-dihydrobenzofuran-4-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 1415470-79-9
• Molecular Formula: C₂₃H₂₇ClO₆
• Molecular Weight: 434.917

Synonyms:(2S,3R,4R,5S,6R)-2-(6-(4-ethylbenzyl)-7-chloro-2,3-dihydrobenzofuran-4-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

Chemical Property of (2S,3R,4R,5S,6R)-2-(6-(4-ethylbenzyl)-7-chloro-2,3-dihydrobenzofuran-4-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

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Technology Process of (2S,3R,4R,5S,6R)-2-(6-(4-ethylbenzyl)-7-chloro-2,3-dihydrobenzofuran-4-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

There total 28 articles about (2S,3R,4R,5S,6R)-2-(6-(4-ethylbenzyl)-7-chloro-2,3-dihydrobenzofuran-4-yl)-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: 8.0%

4-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)-6-(4-ethylbenzyl)-7-chloro-2,3-dihydrobenzofuran → (2S,3R,4R,5S,6R)-2-(6-(4-ethylbenzyl)-7-chloro-2,3-dihydrobenzofuran-4-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol (1415470-79-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20 ℃; for 14h;

Reference yield:

methyl 3-methoxy-2-nitrobenzoate (5307-17-5) → (2S,3R,4R,5S,6R)-2-(6-(4-ethylbenzyl)-7-chloro-2,3-dihydrobenzofuran-4-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol (1415470-79-9)

Guidance literature:

Multi-step reaction with 16 steps

1.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 18 h / 20 °C

2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.5 h / 0 °C

3.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 °C

3.2: 18 h / 0 - 20 °C

4.1: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 0 - 20 °C

5.1: oxalyl dichloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere

6.1: triethylamine / dichloromethane / 18 h / 0 °C / Inert atmosphere

7.1: tetrahydrofuran / 15 h / 0 - 20 °C / Inert atmosphere

8.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

9.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere

9.2: 2 h / -78 °C / Inert atmosphere

10.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / -60 - 20 °C

11.1: sodium thioethylate / N,N-dimethyl-formamide / 6 h / 90 °C

12.1: bromine; acetic acid; triethylamine / 3.15 h / 0 - 20 °C

13.1: potassium carbonate / acetone / 17 h / Reflux

14.1: triphenylphosphine; tetrachloromethane / acetonitrile / 2 h / Reflux

15.1: n-butyllithium / tetrahydrofuran; hexane / 18 h / -78 - 5 °C / Inert atmosphere

16.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 14 h / 20 °C

With hydrogenchloride; triethylsilane; tetrachloromethane; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; palladium 10% on activated carbon; boron trifluoride diethyl etherate; water; hydrogen; bromine; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; sodium hydroxide; sodium nitrite; sodium thioethylate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

Reference yield:

3-methoxy-2-nitrobenzoic acid (4920-80-3) → (2S,3R,4R,5S,6R)-2-(6-(4-ethylbenzyl)-7-chloro-2,3-dihydrobenzofuran-4-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol (1415470-79-9)

Guidance literature:

Multi-step reaction with 17 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C

2.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 18 h / 20 °C

3.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.5 h / 0 °C

4.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 °C

4.2: 18 h / 0 - 20 °C

5.1: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 0 - 20 °C

6.1: oxalyl dichloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere

7.1: triethylamine / dichloromethane / 18 h / 0 °C / Inert atmosphere

8.1: tetrahydrofuran / 15 h / 0 - 20 °C / Inert atmosphere

9.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

10.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere

10.2: 2 h / -78 °C / Inert atmosphere

11.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / -60 - 20 °C

12.1: sodium thioethylate / N,N-dimethyl-formamide / 6 h / 90 °C

13.1: bromine; acetic acid; triethylamine / 3.15 h / 0 - 20 °C

14.1: potassium carbonate / acetone / 17 h / Reflux

15.1: triphenylphosphine; tetrachloromethane / acetonitrile / 2 h / Reflux

16.1: n-butyllithium / tetrahydrofuran; hexane / 18 h / -78 - 5 °C / Inert atmosphere

17.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 14 h / 20 °C

With hydrogenchloride; triethylsilane; tetrachloromethane; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; palladium 10% on activated carbon; boron trifluoride diethyl etherate; water; hydrogen; bromine; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; sodium hydroxide; sodium nitrite; sodium thioethylate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

upstream raw materials:

methyl 3-methoxy-2-nitrobenzoate

3-methoxy-2-nitrobenzoic acid

methyl 2-amino-3-methoxybenzoate

methyl 2-amino-5-bromo-3-methoxy-benzoate

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