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

Base Information

Chemical Name:(2R,3S,4S,4aR,10bS)-9-(4-ethoxybenzyl)-3,4-dihydroxy-2-(hydroxymethyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one
CAS No.:1427370-56-6
Molecular Formula:C₂₂H₂₄O₇
Molecular Weight:400.428
Hs Code.:

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

There total 10 articles about (2R,3S,4S,4aR,10bS)-9-(4-ethoxybenzyl)-3,4-dihydroxy-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: 58.0%

: 1427370-55-5
4-(4-ethoxybenzyl)-2-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl]benzoic acid

: 1427370-56-6
(2R,3S,4S,4aR,10bS)-9-(4-ethoxybenzyl)-3,4-dihydroxy-2-(hydroxymethyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one

Guidance literature:: With hydrogen; palladium dichloride; In methanol; ethyl acetate; for 16h; under 2250.23 Torr; Inert atmosphere;

Reference yield:

: 1427370-54-4
4-(4-ethoxybenzyl)-2-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl]benzenemethanol

: 1427370-56-6
(2R,3S,4S,4aR,10bS)-9-(4-ethoxybenzyl)-3,4-dihydroxy-2-(hydroxymethyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one

Guidance literature:: Multi-step reaction with 2 steps

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

2: hydrogen; palladium dichloride / ethyl acetate; methanol / 16 h / 2250.23 Torr / Inert atmosphere

With Jones reagent; hydrogen; palladium dichloride; In methanol; ethyl acetate; acetone;

Reference yield:

: 957228-84-1
2-bromo-4-(4-ethoxybenzyl)benzenemethanol

: 1427370-56-6
(2R,3S,4S,4aR,10bS)-9-(4-ethoxybenzyl)-3,4-dihydroxy-2-(hydroxymethyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 - -5 °C / Inert atmosphere

2.3: 2 h / -25 - 5 °C / Inert atmosphere

3.1: acetic acid; sodium acetate; palladium dichloride / water / 1.33 h / 70 °C

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

5.1: hydrogen; palladium dichloride / ethyl acetate; methanol / 16 h / 2250.23 Torr / Inert atmosphere

With Jones reagent; n-butyllithium; hydrogen; sodium acetate; sodium hydride; acetic acid; palladium dichloride; In tetrahydrofuran; methanol; hexane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; mineral oil;