(2R,3S,4S,4aR,10bS)-8-chloro-3,4-dihydroxy-2-(hydroxymethyl)-9-(4-methoxybenzyl)-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-2-(hydroxymethyl)-9-(4-methoxybenzyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one
CAS No.:1428730-79-3
Molecular Formula:C₂₁H₂₁ClO₇
Molecular Weight:420.847
Hs Code.:

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

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

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

There total 13 articles about (2R,3S,4S,4aR,10bS)-8-chloro-3,4-dihydroxy-2-(hydroxymethyl)-9-(4-methoxybenzyl)-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: 40.0%

: 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

: 74-88-4
methyl iodide

: 1428730-79-3
(2R,3S,4S,4aR,10bS)-8-chloro-3,4-dihydroxy-2-(hydroxymethyl)-9-(4-methoxybenzyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one

Guidance literature:: With potassium carbonate; In acetone; at 20 ℃; for 60h;

Reference yield:

: 474330-54-6
5-amino-2-bromo-4-methylbenzoic acid methyl ester

: 1428730-79-3
(2R,3S,4S,4aR,10bS)-8-chloro-3,4-dihydroxy-2-(hydroxymethyl)-9-(4-methoxybenzyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: sodium nitrite; hydrogenchloride / water; 1,4-dioxane / 2 h / -10 - 0 °C

1.2: 0.67 h / 0 - 20 °C

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

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

3.2: 1 h / -10 - 50 °C / Inert atmosphere

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

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

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

6.2: 0 - 20 °C / Inert atmosphere

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

7.2: 3 h / -78 - -25 °C / Inert atmosphere

7.3: 3 h / -25 - 5 °C / Inert atmosphere

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

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

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

11.1: potassium carbonate / acetone / 60 h / 20 °C

With hydrogenchloride; 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; potassium carbonate; acetic acid; N,N-dimethyl-formamide; trifluoroacetic acid; palladium dichloride; sodium nitrite; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;

Reference yield:

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

: 1428730-79-3
(2R,3S,4S,4aR,10bS)-8-chloro-3,4-dihydroxy-2-(hydroxymethyl)-9-(4-methoxybenzyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one

Guidance literature:: Multi-step reaction with 10 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

10.1: potassium carbonate / acetone / 60 h / 20 °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; potassium carbonate; acetic acid; N,N-dimethyl-formamide; trifluoroacetic acid; palladium dichloride; In tetrahydrofuran; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;