Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-(3-iodoindol-2-yl)-2-<2-(phenylsulfonyl)prop-2-enyl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

Base Information

Chemical Name:Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-(3-iodoindol-2-yl)-2-<2-(phenylsulfonyl)prop-2-enyl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate
CAS No.:133399-33-4
Molecular Formula:C₂₉H₃₁IN₂O₆S
Molecular Weight:662.545
Hs Code.:

Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-(3-iodoindol-2-yl)-2-<2-(phenylsulfonyl)prop-2-enyl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

Synonyms:Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-(3-iodoindol-2-yl)-2-<2-(phenylsulfonyl)prop-2-enyl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

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Chemical Property of Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-(3-iodoindol-2-yl)-2-<2-(phenylsulfonyl)prop-2-enyl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

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Technology Process of Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-(3-iodoindol-2-yl)-2-<2-(phenylsulfonyl)prop-2-enyl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

There total 7 articles about Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-(3-iodoindol-2-yl)-2-<2-(phenylsulfonyl)prop-2-enyl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate 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: 81.0%

: 133372-45-9
Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-indol-2-yl-2-<2-(phenylsulfonyl)prop-2-enyl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

: 133399-33-4
Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-(3-iodoindol-2-yl)-2-<2-(phenylsulfonyl)prop-2-enyl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

Guidance literature:: With N-iodo-succinimide; In acetone; for 0.25h; Ambient temperature;
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

: 133399-33-4
Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-(3-iodoindol-2-yl)-2-<2-(phenylsulfonyl)prop-2-enyl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

Guidance literature:: Multi-step reaction with 5 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

With disodium hydrogenphosphate; N-iodo-succinimide; sodium amalgam; sodium carbonate; toluene-4-sulfonic acid; cyclohexa-1,3-diene; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; acetone;
DOI:10.1021/jo00311a022

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

: 133399-33-4
Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-(3-iodoindol-2-yl)-2-<2-(phenylsulfonyl)prop-2-enyl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

Guidance literature:: Multi-step reaction with 6 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

With disodium hydrogenphosphate; N-iodo-succinimide; osmium(VIII) oxide; sodium amalgam; water; 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