(2S,3R,4R,5S,6R)-2-(8-chloro-7-(4-ethylbenzyl)chroman-5-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

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Chemical Name:(2S,3R,4R,5S,6R)-2-(8-chloro-7-(4-ethylbenzyl)chroman-5-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
CAS No.:1415470-82-4
Molecular Formula:C₂₄H₂₉ClO₆
Molecular Weight:448.944
Hs Code.:

Synonyms:(2S,3R,4R,5S,6R)-2-(8-chloro-7-(4-ethylbenzyl)chroman-5-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

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Chemical Property of (2S,3R,4R,5S,6R)-2-(8-chloro-7-(4-ethylbenzyl)chroman-5-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

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Technology Process of (2S,3R,4R,5S,6R)-2-(8-chloro-7-(4-ethylbenzyl)chroman-5-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

There total 22 articles about (2S,3R,4R,5S,6R)-2-(8-chloro-7-(4-ethylbenzyl)chroman-5-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: 28.0%

: 8-chloro-7-(4-ethylbenzyl)-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)-2H-chromene

: 1415470-82-4
(2S,3R,4R,5S,6R)-2-(8-chloro-7-(4-ethylbenzyl)chroman-5-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20 ℃; for 6h;

Reference yield:

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

: 1415470-82-4
(2S,3R,4R,5S,6R)-2-(8-chloro-7-(4-ethylbenzyl)chroman-5-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 10 steps

1: sodium hydride / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 16 h / 0 - 20 °C / Inert atmosphere

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

3: bromine; acetic acid; triethylamine / 15.15 h / 0 - 20 °C

4: potassium carbonate / acetone / 15 h / 0 - 50 °C

5: triphenylphosphine; tetrachloromethane / acetonitrile / 3 h / 0 - 55 °C

6: n-butyllithium / tetrahydrofuran; hexane / 18 h / -78 - 10 °C / Inert atmosphere

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

8: potassium carbonate / acetone / 18 h / Reflux

9: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 3 h / 20 °C

10: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 6 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrachloromethane; n-butyllithium; palladium 10% on activated carbon; hydrogen; bromine; sodium hydride; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; sodium thioethylate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; mineral oil;

Reference yield:

: 697762-67-7
methyl 5-bromo-2-chloro-3-methoxybenzoate

: 1415470-82-4
(2S,3R,4R,5S,6R)-2-(8-chloro-7-(4-ethylbenzyl)chroman-5-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 19 steps

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

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

3.1: dichloromethane / 0.08 h / 0 °C

3.2: 15.5 h / 0 - 20 °C

4.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 15 h / 0 - 20 °C

5.1: n-butyllithium / tetrahydrofuran; toluene / 0.67 h / -78 °C / Inert atmosphere

5.2: 1 h / -78 °C / Inert atmosphere

6.1: sodium hydrogencarbonate / water; methanol / 0.5 h / -78 - 20 °C

7.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 2 h / -50 - 0 °C

8.1: triethylamine; dmap / dichloromethane / 15.15 h / 0 - 20 °C

9.1: sodium methylate; methanol / 1 h / 20 °C

10.1: sodium hydride / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 16 h / 0 - 20 °C / Inert atmosphere

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

12.1: bromine; acetic acid; triethylamine / 15.15 h / 0 - 20 °C

13.1: potassium carbonate / acetone / 15 h / 0 - 50 °C

14.1: triphenylphosphine; tetrachloromethane / acetonitrile / 3 h / 0 - 55 °C

15.1: n-butyllithium / tetrahydrofuran; hexane / 18 h / -78 - 10 °C / Inert atmosphere

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

17.1: potassium carbonate / acetone / 18 h / Reflux

18.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 3 h / 20 °C

19.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 6 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; methanol; triethylsilane; tetrachloromethane; dmap; n-butyllithium; oxalyl dichloride; palladium 10% on activated carbon; boron trifluoride diethyl etherate; water; hydrogen; bromine; sodium methylate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; sodium hydroxide; sodium thioethylate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil;