(+/-)-16-carbomethoxy-20-deethyl-1-(phenylsulfonyl)-15-oxo-20,21-didehydrocleavamine

Base Information

Chemical Name:(+/-)-16-carbomethoxy-20-deethyl-1-(phenylsulfonyl)-15-oxo-20,21-didehydrocleavamine
CAS No.:108713-42-4
Molecular Formula:C₂₅H₂₄N₂O₅S
Molecular Weight:464.542
Hs Code.:

Synonyms:

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Chemical Property of (+/-)-16-carbomethoxy-20-deethyl-1-(phenylsulfonyl)-15-oxo-20,21-didehydrocleavamine

Chemical Property:

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Technology Process of (+/-)-16-carbomethoxy-20-deethyl-1-(phenylsulfonyl)-15-oxo-20,21-didehydrocleavamine

There total 10 articles about (+/-)-16-carbomethoxy-20-deethyl-1-(phenylsulfonyl)-15-oxo-20,21-didehydrocleavamine 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:

: 108713-16-2
methyl 2-<(benzyloxy)carbonyl>-6-exo-<1-(phenylsulfonyl)indol-2-yl>-8-methoxy-2-azabicyclo<2.2.2>oct-7-ene-6-endo-carboxylate

: 108713-42-4,108814-47-7
(+/-)-16-carbomethoxy-20-deethyl-1-(phenylsulfonyl)-15-oxo-20,21-didehydrocleavamine

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / trimethylsilyl iodide / CH₂Cl₂ / 4 h / 0 °C

2: 70 percent / 72 h / 25 °C

3: 295 mg / oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h

4: 30 mg / titanium tetrachloride / CH₂Cl₂ / 6 h / 25 °C

5: 85 mg / acetic acid, sodium acetate, sodium cyanoborohydride / tetrahydrofuran / 4 h / 25 °C

6: 1.) LDA / 1.) THF, hexane, 10 min, 2.) THF, hexane, 0 deg C, 6 h

With oxalyl dichloride; trimethylsilyl iodide; sodium acetate; titanium tetrachloride; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00390a034

Reference yield:

: 108713-17-3,108813-37-2
methyl 2-<(benzyloxy)carbonyl>-8-oxo-6-exo-<1-(phenylsulfonyl)indol-2-yl>-8-methoxy-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

: 108713-42-4,108814-47-7
(+/-)-16-carbomethoxy-20-deethyl-1-(phenylsulfonyl)-15-oxo-20,21-didehydrocleavamine

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / cyclohexadiene, trifluoroacetic acid / 10percent Pd/C / methanol; H₂O / 1 h / 25 °C

2: 70 percent / 72 h / 25 °C

3: 295 mg / oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h

4: 30 mg / titanium tetrachloride / CH₂Cl₂ / 6 h / 25 °C

5: 85 mg / acetic acid, sodium acetate, sodium cyanoborohydride / tetrahydrofuran / 4 h / 25 °C

6: 1.) LDA / 1.) THF, hexane, 10 min, 2.) THF, hexane, 0 deg C, 6 h

With oxalyl dichloride; sodium acetate; titanium tetrachloride; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; cyclohexa-1,3-diene; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jo00390a034

Reference yield:

: 108713-18-4
methyl 8-oxo-6-exo-<1-(phenylsulfonyl)indol-2-yl>-8-methoxy-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

: 108713-42-4,108814-47-7
(+/-)-16-carbomethoxy-20-deethyl-1-(phenylsulfonyl)-15-oxo-20,21-didehydrocleavamine

Guidance literature:: Multi-step reaction with 5 steps

1: 70 percent / 72 h / 25 °C

2: 295 mg / oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h

3: 30 mg / titanium tetrachloride / CH₂Cl₂ / 6 h / 25 °C

4: 85 mg / acetic acid, sodium acetate, sodium cyanoborohydride / tetrahydrofuran / 4 h / 25 °C

5: 1.) LDA / 1.) THF, hexane, 10 min, 2.) THF, hexane, 0 deg C, 6 h

With oxalyl dichloride; sodium acetate; titanium tetrachloride; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00390a034