(2R,3S,4S,4aR,10bS)-8-chloro-3,4-dihydroxy-9-(4-hydroxybenzyl)-2-(hydroxymethyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one

Base Information

Chemical Name:(2R,3S,4S,4aR,10bS)-8-chloro-3,4-dihydroxy-9-(4-hydroxybenzyl)-2-(hydroxymethyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one
CAS No.:1428730-78-2
Molecular Formula:C₂₀H₁₉ClO₇
Molecular Weight:406.82
Hs Code.:

Synonyms:(2R,3S,4S,4aR,10bS)-8-chloro-3,4-dihydroxy-9-(4-hydroxybenzyl)-2-(hydroxymethyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3S,4S,4aR,10bS)-8-chloro-3,4-dihydroxy-9-(4-hydroxybenzyl)-2-(hydroxymethyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (2R,3S,4S,4aR,10bS)-8-chloro-3,4-dihydroxy-9-(4-hydroxybenzyl)-2-(hydroxymethyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one

There total 12 articles about (2R,3S,4S,4aR,10bS)-8-chloro-3,4-dihydroxy-9-(4-hydroxybenzyl)-2-(hydroxymethyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one 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: 47.0%

: 1427370-48-6
5-chloro-4-(4-ethoxybenzyl)-2-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl]benzoic acid

: 1428730-78-2
(2R,3S,4S,4aR,10bS)-8-chloro-3,4-dihydroxy-9-(4-hydroxybenzyl)-2-(hydroxymethyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one

Guidance literature:: With boron tribromide; In dichloromethane; at 0 ℃; for 0.5h;

Reference yield:

: 1061314-02-0
2-bromo-5-chloro-4-methyl-benzoic acid methyl ester

: 1428730-78-2
(2R,3S,4S,4aR,10bS)-8-chloro-3,4-dihydroxy-9-(4-hydroxybenzyl)-2-(hydroxymethyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: tetrabutylammomium bromide; ruthenium(III) chloride trihydrate; sodium hypochlorite / 1,2-dichloro-ethane / 6 h / pH 9

2.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 50 °C

2.2: 1 h / -10 - 50 °C / Inert atmosphere

3.1: trifluoroacetic acid; triethylsilane; trifluorormethanesulfonic acid / 3 h / 20 - 75 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

5.2: 0 - 20 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

6.2: 3 h / -78 - -25 °C / Inert atmosphere

6.3: 3 h / -25 - 5 °C / Inert atmosphere

7.1: acetic acid; sodium acetate; palladium dichloride / water / 2 h / 20 - 75 °C

8.1: Jones reagent / acetone / 6 h / 0 - 20 °C

9.1: boron tribromide / dichloromethane / 0.5 h / 0 °C

With triethylsilane; sodium hypochlorite; lithium aluminium tetrahydride; Jones reagent; n-butyllithium; thionyl chloride; trifluorormethanesulfonic acid; ruthenium(III) chloride trihydrate; tetrabutylammomium bromide; sodium acetate; boron tribromide; sodium hydride; acetic acid; N,N-dimethyl-formamide; trifluoroacetic acid; palladium dichloride; In tetrahydrofuran; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;

Reference yield:

: 1061314-04-2
5-bromo-2-chloro-4-(methoxycarbonyl)benzoic acid

: 1428730-78-2
(2R,3S,4S,4aR,10bS)-8-chloro-3,4-dihydroxy-9-(4-hydroxybenzyl)-2-(hydroxymethyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 50 °C

1.2: 1 h / -10 - 50 °C / Inert atmosphere

2.1: trifluoroacetic acid; triethylsilane; trifluorormethanesulfonic acid / 3 h / 20 - 75 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

5.2: 3 h / -78 - -25 °C / Inert atmosphere

5.3: 3 h / -25 - 5 °C / Inert atmosphere

6.1: acetic acid; sodium acetate; palladium dichloride / water / 2 h / 20 - 75 °C

7.1: Jones reagent / acetone / 6 h / 0 - 20 °C

8.1: boron tribromide / dichloromethane / 0.5 h / 0 °C

With triethylsilane; lithium aluminium tetrahydride; Jones reagent; n-butyllithium; thionyl chloride; trifluorormethanesulfonic acid; sodium acetate; boron tribromide; sodium hydride; acetic acid; N,N-dimethyl-formamide; trifluoroacetic acid; palladium dichloride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone;