7-Ethyl-10-hydroxy-18-nor-20-(phenylselenyl)camptothecin

Base Information

Chemical Name:7-Ethyl-10-hydroxy-18-nor-20-(phenylselenyl)camptothecin
CAS No.:178949-38-7
Molecular Formula:C₂₇H₂₂N₂O₄Se
Molecular Weight:517.443
Hs Code.:

Synonyms:7-Ethyl-10-hydroxy-18-nor-20-(phenylselenyl)camptothecin

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Chemical Property of 7-Ethyl-10-hydroxy-18-nor-20-(phenylselenyl)camptothecin

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Technology Process of 7-Ethyl-10-hydroxy-18-nor-20-(phenylselenyl)camptothecin

There total 11 articles about 7-Ethyl-10-hydroxy-18-nor-20-(phenylselenyl)camptothecin 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:

: 159021-79-1
[3-Hydroxy-pyrrolidin-(2Z)-ylidene]-acetic acid methyl ester

: 178949-38-7
7-Ethyl-10-hydroxy-18-nor-20-(phenylselenyl)camptothecin

Guidance literature:: Multi-step reaction with 9 steps

1: 73 percent / Et₃N / ethanol / 72 h / Ambient temperature

2: 88 percent / NBS / dimethylformamide / 20 h / Ambient temperature

3: 64 percent / Et₃N / palladium(II) acetate, tri-o-tolylphosphine / acetonitrile / 3 h / 125 °C / 3878.6 Torr

4: 90 percent / LiHMDS / tetrahydrofuran / 1.) -78 deg C, 1.25 h, 2.) -78 deg C to r.t., 15 h

6: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

7: 70 percent / p-toluenesulfonic acid / toluene / 15 h / Heating

8: 54 percent / 48percent aq. HBr / 14 h / 130 °C

9: pyridine / 24 h

With pyridine; N-Bromosuccinimide; hydrogen bromide; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; lithium hexamethyldisilazane; palladium diacetate; tris-(o-tolyl)phosphine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo00102a030

Reference yield:

: 159021-78-0
Acetic acid 2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-pyrrolidin-3-yl ester

: 178949-38-7
7-Ethyl-10-hydroxy-18-nor-20-(phenylselenyl)camptothecin

Guidance literature:: Multi-step reaction with 10 steps

1: 81 percent / NaOMe / 17 h / Heating

2: 73 percent / Et₃N / ethanol / 72 h / Ambient temperature

3: 88 percent / NBS / dimethylformamide / 20 h / Ambient temperature

4: 64 percent / Et₃N / palladium(II) acetate, tri-o-tolylphosphine / acetonitrile / 3 h / 125 °C / 3878.6 Torr

5: 90 percent / LiHMDS / tetrahydrofuran / 1.) -78 deg C, 1.25 h, 2.) -78 deg C to r.t., 15 h

7: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

8: 70 percent / p-toluenesulfonic acid / toluene / 15 h / Heating

9: 54 percent / 48percent aq. HBr / 14 h / 130 °C

10: pyridine / 24 h

With pyridine; N-Bromosuccinimide; hydrogen bromide; sodium methylate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; lithium hexamethyldisilazane; palladium diacetate; tris-(o-tolyl)phosphine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo00102a030

Reference yield:

: 178949-26-3
1-Hydroxy-7-methoxycarbonylmethyl-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid methyl ester

: 178949-38-7
7-Ethyl-10-hydroxy-18-nor-20-(phenylselenyl)camptothecin

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / NBS / dimethylformamide / 20 h / Ambient temperature

2: 64 percent / Et₃N / palladium(II) acetate, tri-o-tolylphosphine / acetonitrile / 3 h / 125 °C / 3878.6 Torr

3: 90 percent / LiHMDS / tetrahydrofuran / 1.) -78 deg C, 1.25 h, 2.) -78 deg C to r.t., 15 h

5: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

6: 70 percent / p-toluenesulfonic acid / toluene / 15 h / Heating

7: 54 percent / 48percent aq. HBr / 14 h / 130 °C

8: pyridine / 24 h

With pyridine; N-Bromosuccinimide; hydrogen bromide; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; lithium hexamethyldisilazane; palladium diacetate; tris-(o-tolyl)phosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo00102a030