(4aR,5R,6R,11bR)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-5-vinyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene

Base Information

Chemical Name:(4aR,5R,6R,11bR)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-5-vinyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene
CAS No.:683805-27-8
Molecular Formula:C₂₆H₃₀O₇
Molecular Weight:454.52
Hs Code.:

Synonyms:(4aR,5R,6R,11bR)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-5-vinyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene

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Chemical Property of (4aR,5R,6R,11bR)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-5-vinyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene

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Technology Process of (4aR,5R,6R,11bR)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-5-vinyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene

There total 5 articles about (4aR,5R,6R,11bR)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-5-vinyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene 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: 86.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 683805-26-7
(4aR,5R,6R,11bR)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carbaldehyde

: 683805-27-8
(4aR,5R,6R,11bR)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-5-vinyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

(4aR,5R,6R,11bR)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carbaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 45h; Further stages.;
DOI:10.1016/j.tet.2004.01.017

Reference yield:

: 518-28-5
podofilox

: 683805-27-8
(4aR,5R,6R,11bR)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-5-vinyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 60 percent / LAH / tetrahydrofuran / 2.5 h / 0 °C

2.1: p-toluenesulfonic acid monohydrate / 3.5 h / 20 °C

2.2: 54 percent / Et₃N / methanol; H₂O / 8 h / 60 °C

3.1: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

4.1: n-butyl lithium / tetrahydrofuran; hexane / 0.08 h / -78 °C

4.2: 86 percent / tetrahydrofuran; hexane / 45 h / -78 °C

With lithium aluminium tetrahydride; n-butyllithium; Dess-Martin periodane; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; 3.1: Dess-Martin oxidation / 4.2: Wittig reaction;
DOI:10.1016/j.tet.2004.01.017

Reference yield:

: 78339-51-2
podophyllol

: 683805-27-8
(4aR,5R,6R,11bR)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-5-vinyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene

Guidance literature:: Multi-step reaction with 3 steps

1.1: p-toluenesulfonic acid monohydrate / 3.5 h / 20 °C

1.2: 54 percent / Et₃N / methanol; H₂O / 8 h / 60 °C

2.1: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

3.1: n-butyl lithium / tetrahydrofuran; hexane / 0.08 h / -78 °C

3.2: 86 percent / tetrahydrofuran; hexane / 45 h / -78 °C

With n-butyllithium; Dess-Martin periodane; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; 2.1: Dess-Martin oxidation / 3.2: Wittig reaction;
DOI:10.1016/j.tet.2004.01.017