20-Deethyl-15,20-exo,exo-dihydroxy-5a-(phenylsulfonyl)-5,6-homocoronaridine

Base Information

Chemical Name:20-Deethyl-15,20-exo,exo-dihydroxy-5a-(phenylsulfonyl)-5,6-homocoronaridine
CAS No.:133372-46-0
Molecular Formula:C₂₉H₃₂N₂O₆S
Molecular Weight:536.649
Hs Code.:

Synonyms:

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Chemical Property of 20-Deethyl-15,20-exo,exo-dihydroxy-5a-(phenylsulfonyl)-5,6-homocoronaridine

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Technology Process of 20-Deethyl-15,20-exo,exo-dihydroxy-5a-(phenylsulfonyl)-5,6-homocoronaridine

There total 8 articles about 20-Deethyl-15,20-exo,exo-dihydroxy-5a-(phenylsulfonyl)-5,6-homocoronaridine 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:

: 79328-88-4
methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate

: 133372-46-0,133372-47-1
20-Deethyl-15,20-exo,exo-dihydroxy-5a-(phenylsulfonyl)-5,6-homocoronaridine

Guidance literature:: Multi-step reaction with 7 steps

1: 86 percent / H₂O, 4-methylmorpholine N-oxide, OsO₄ / tetrahydrofuran / 12 h

2: 87 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h

3: 85 percent / cyclohexadiene, TFA / Pd / C / methanol / 12 h

4: 79 percent / Na₂HPO₄, 5percent Na-Hg-amalgam / methanol / Ambient temperature

5: 85 percent / Na₂CO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 81 percent / N-iodosuccinimide / acetone / 0.25 h / Ambient temperature

7: 1) AIBN, 2) Bu₃SnH / 1) benzene, reflux, 2) benzene, reflux, 20 min

With disodium hydrogenphosphate; N-iodo-succinimide; osmium(VIII) oxide; sodium amalgam; 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride; sodium carbonate; toluene-4-sulfonic acid; cyclohexa-1,3-diene; 4-methylmorpholine N-oxide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone;
DOI:10.1021/jo00311a022

Reference yield:

: 133372-42-6
Isopropylidene Derivative of Methyl 2-(Benzyloxycarbonyl)-7,8-exo,exo-dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

: 133372-46-0,133372-47-1
20-Deethyl-15,20-exo,exo-dihydroxy-5a-(phenylsulfonyl)-5,6-homocoronaridine

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / cyclohexadiene, TFA / Pd / C / methanol / 12 h

2: 79 percent / Na₂HPO₄, 5percent Na-Hg-amalgam / methanol / Ambient temperature

3: 85 percent / Na₂CO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 81 percent / N-iodosuccinimide / acetone / 0.25 h / Ambient temperature

5: 1) AIBN, 2) Bu₃SnH / 1) benzene, reflux, 2) benzene, reflux, 20 min

With disodium hydrogenphosphate; N-iodo-succinimide; sodium amalgam; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium carbonate; cyclohexa-1,3-diene; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; acetone;
DOI:10.1021/jo00311a022

Reference yield:

: 133372-41-5
Methyl 2-(Benzyloxycarbonyl)-7,8-exo,exo-dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

: 133372-46-0,133372-47-1
20-Deethyl-15,20-exo,exo-dihydroxy-5a-(phenylsulfonyl)-5,6-homocoronaridine

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h

2: 85 percent / cyclohexadiene, TFA / Pd / C / methanol / 12 h

3: 79 percent / Na₂HPO₄, 5percent Na-Hg-amalgam / methanol / Ambient temperature

4: 85 percent / Na₂CO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 81 percent / N-iodosuccinimide / acetone / 0.25 h / Ambient temperature

6: 1) AIBN, 2) Bu₃SnH / 1) benzene, reflux, 2) benzene, reflux, 20 min

With disodium hydrogenphosphate; N-iodo-succinimide; sodium amalgam; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium carbonate; toluene-4-sulfonic acid; cyclohexa-1,3-diene; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; acetone;
DOI:10.1021/jo00311a022