[(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

Base Information

Chemical Name:[(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
CAS No.:683805-45-0
Molecular Formula:C₂₅H₂₇NO₇
Molecular Weight:453.492
Hs Code.:

[(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

Synonyms:[(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

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Chemical Property of [(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

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Technology Process of [(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

There total 5 articles about [(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 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:

: 6559-91-7
4'-demethylepipodophyllotoxin

: 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

Guidance literature:: Multi-step reaction with 5 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

With 1H-imidazole; lithium aluminium tetrahydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; 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

: 683805-45-0
[(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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 683805-43-8
8-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-6,7-bis-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-5-ol

: 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

Guidance literature:: Multi-step reaction with 3 steps

1: 901 mg / p-toluenesulfonic acid monohydrate / 0.58 h / 20 °C

2: Et₃N / CH₂Cl₂ / 0.83 h / 0 °C

3: 345.6 mg / dimethylformamide / 5 h / 85 °C

With toluene-4-sulfonic acid; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.01.017