2-[(4aR,5R,6R,11bS)-6-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,2-dimethyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthren-5-yl]-acetamide

Base Information

Chemical Name:2-[(4aR,5R,6R,11bS)-6-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,2-dimethyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthren-5-yl]-acetamide
CAS No.:683805-46-1
Molecular Formula:C₂₅H₂₉NO₈
Molecular Weight:471.507
Hs Code.:

2-[(4aR,5R,6R,11bS)-6-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,2-dimethyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthren-5-yl]-acetamide

Synonyms:2-[(4aR,5R,6R,11bS)-6-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,2-dimethyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthren-5-yl]-acetamide

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Chemical Property of 2-[(4aR,5R,6R,11bS)-6-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,2-dimethyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthren-5-yl]-acetamide

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Technology Process of 2-[(4aR,5R,6R,11bS)-6-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,2-dimethyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthren-5-yl]-acetamide

There total 6 articles about 2-[(4aR,5R,6R,11bS)-6-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,2-dimethyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthren-5-yl]-acetamide 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: 44.0%

: 683805-45-0
[(4aR,5R,6R,11bS)-6-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,2-dimethyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthren-5-yl]-acetonitrile

: 683805-46-1
2-[(4aR,5R,6R,11bS)-6-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,2-dimethyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthren-5-yl]-acetamide

Guidance literature:: With sodium hydroxide; In ethanol; at 75 ℃; for 28h;
DOI:10.1016/j.tet.2004.01.017

Reference yield:

: 6559-91-7
4'-demethylepipodophyllotoxin

: 683805-46-1
2-[(4aR,5R,6R,11bS)-6-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,2-dimethyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthren-5-yl]-acetamide

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

2: 51 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

3: 901 mg / p-toluenesulfonic acid monohydrate / 0.58 h / 20 °C

4: Et₃N / CH₂Cl₂ / 0.83 h / 0 °C

5: 345.6 mg / dimethylformamide / 5 h / 85 °C

6: 44 percent / NaOH / ethanol / 28 h / 75 °C

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.01.017

Reference yield:

: 118356-07-3
4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-epipodophyllotoxin

: 683805-46-1
2-[(4aR,5R,6R,11bS)-6-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,2-dimethyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthren-5-yl]-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: 51 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

2: 901 mg / p-toluenesulfonic acid monohydrate / 0.58 h / 20 °C

3: Et₃N / CH₂Cl₂ / 0.83 h / 0 °C

4: 345.6 mg / dimethylformamide / 5 h / 85 °C

5: 44 percent / NaOH / ethanol / 28 h / 75 °C

With sodium hydroxide; lithium aluminium tetrahydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.01.017