(-)-8-des-ethyl,(8S)-phenylseleno-13-epituberostemonine

Base Information

Chemical Name:(-)-8-des-ethyl,(8S)-phenylseleno-13-epituberostemonine
CAS No.:828921-50-2
Molecular Formula:C₂₆H₃₃NO₄Se
Molecular Weight:502.512
Hs Code.:

Synonyms:(-)-8-des-ethyl,(8S)-phenylseleno-13-epituberostemonine

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Chemical Property of (-)-8-des-ethyl,(8S)-phenylseleno-13-epituberostemonine

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Technology Process of (-)-8-des-ethyl,(8S)-phenylseleno-13-epituberostemonine

There total 19 articles about (-)-8-des-ethyl,(8S)-phenylseleno-13-epituberostemonine 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%

: 5707-04-0
Phenylselenyl chloride

: 828921-47-7
N,N-dimethyl-2R,S-[2S-(4S-methyl-5-oxotetrahydrofuran-2-yl)-(1,2S,4,5,6,7,7aS,8S,10aR,10bS)-decahydroazepino[3,2,1-hi]indol-10-yl]propionamide

: 828921-50-2
(-)-8-des-ethyl,(8S)-phenylseleno-13-epituberostemonine

Guidance literature:: In water; acetonitrile; at 0 ℃; for 18h;
DOI:10.1021/ja044280k

Reference yield:

: 144534-49-6
(2S,3aR,7aR)-3a-hydroxy-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 828921-50-2
(-)-8-des-ethyl,(8S)-phenylseleno-13-epituberostemonine

Guidance literature:: Multi-step reaction with 20 steps

1.1: 26 g / dimethylaminopyridine; pyridine / CH₂Cl₂ / 20 h / Heating

2.1: 97 percent / cerium(III) chloride heptahydrate; NaBH₄ / tetrahydrofuran; methanol / 15 h / 0 °C

3.1: 93 percent / Pd₂(dba)3*CHCl₃; tribenzylphosphine; triethylamine / formic acid / tetrahydrofuran / 16 h / Heating

4.1: 97 percent / imidazole; dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

5.1: 90 percent / triethylsilane; palladium(II) acetate; triethylamine / CH₂Cl₂ / 15 h / 20 °C

6.1: 96 percent / K₂CO₃ / toluene / 15 h / 60 °C

7.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

8.1: 88 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 15 h / 20 °C

9.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 0.08 h / -90 °C

9.2: 66 percent / tetrahydrofuran / 0.5 h / -90 °C

10.1: 92 percent / Grubb's 2nd generation catalyst / CH₂Cl₂ / 2 h / Heating

11.1: 91 percent / triethylamine / CH₂Cl₂ / 3 h / 20 °C

12.1: chlorotris(triphenylphosphine)rhodium(I); H₂ / CH₂Cl₂; ethanol / 15 h / 20 °C / 760 Torr

12.2: 89 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 3.5 h / 20 °C

13.1: cerium(III) chloride heptahydrate; sodium borohydride / tetrahydrofuran; methanol / 0.17 h / 0 °C

14.1: 1.0 g / imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 14 h / 20 °C

15.1: dimethylaluminum chloride / CH₂Cl₂; hexane / 1 h / 20 °C

15.2: 94 percent / CH₂Cl₂; hexane / 14 h / 20 °C

16.1: 4,4'-di-tert-butylbiphenyl; lithium / tetrahydrofuran / 0.5 h / -78 °C

16.2: 95 percent / tetrahydrofuran / 0.25 h / -78 °C

17.1: 80 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 17 h / -78 - -15 °C

18.1: 388 mg / p-toluenesulfonic acid monohydrate / methanol / 20 h / 20 °C

19.1: 65 percent / xylene / 19 h / 130 - 140 °C

20.1: 81 percent / acetonitrile; H₂O / 18 h / 0 °C

With pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; triethylsilane; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; Wilkinson's catalyst; cerium(III) chloride; tetrapropylammonium perruthennate; 4,4'-di-tert-butylbiphenyl; tetrabutyl ammonium fluoride; hydrogen; palladium diacetate; dimethylaluminum chloride; lithium; potassium hexamethylsilazane; L-Selectride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; tribenzylphosphine; formic acid; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; toluene; acetonitrile; xylene; 2.1: Luche reduction / 13.1: Luche reduction / 19.1: Eschenmoser-Claisen rearrangement;
DOI:10.1021/ja044280k

Reference yield:

: 171523-63-0
<2S-(2β,3aβ,7aβ)>-2,3,3a,6,7,7a-hexahydro-3a-benzoyloxy-6-oxo-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester

: 828921-50-2
(-)-8-des-ethyl,(8S)-phenylseleno-13-epituberostemonine

Guidance literature:: Multi-step reaction with 19 steps

1.1: 97 percent / cerium(III) chloride heptahydrate; NaBH₄ / tetrahydrofuran; methanol / 15 h / 0 °C

2.1: 93 percent / Pd₂(dba)3*CHCl₃; tribenzylphosphine; triethylamine / formic acid / tetrahydrofuran / 16 h / Heating

3.1: 97 percent / imidazole; dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

4.1: 90 percent / triethylsilane; palladium(II) acetate; triethylamine / CH₂Cl₂ / 15 h / 20 °C

5.1: 96 percent / K₂CO₃ / toluene / 15 h / 60 °C

6.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

7.1: 88 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 15 h / 20 °C

8.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 0.08 h / -90 °C

8.2: 66 percent / tetrahydrofuran / 0.5 h / -90 °C

9.1: 92 percent / Grubb's 2nd generation catalyst / CH₂Cl₂ / 2 h / Heating

10.1: 91 percent / triethylamine / CH₂Cl₂ / 3 h / 20 °C

11.1: chlorotris(triphenylphosphine)rhodium(I); H₂ / CH₂Cl₂; ethanol / 15 h / 20 °C / 760 Torr

11.2: 89 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 3.5 h / 20 °C

12.1: cerium(III) chloride heptahydrate; sodium borohydride / tetrahydrofuran; methanol / 0.17 h / 0 °C

13.1: 1.0 g / imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 14 h / 20 °C

14.1: dimethylaluminum chloride / CH₂Cl₂; hexane / 1 h / 20 °C

14.2: 94 percent / CH₂Cl₂; hexane / 14 h / 20 °C

15.1: 4,4'-di-tert-butylbiphenyl; lithium / tetrahydrofuran / 0.5 h / -78 °C

15.2: 95 percent / tetrahydrofuran / 0.25 h / -78 °C

16.1: 80 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 17 h / -78 - -15 °C

17.1: 388 mg / p-toluenesulfonic acid monohydrate / methanol / 20 h / 20 °C

18.1: 65 percent / xylene / 19 h / 130 - 140 °C

19.1: 81 percent / acetonitrile; H₂O / 18 h / 0 °C

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; triethylsilane; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; Wilkinson's catalyst; cerium(III) chloride; tetrapropylammonium perruthennate; 4,4'-di-tert-butylbiphenyl; tetrabutyl ammonium fluoride; hydrogen; palladium diacetate; dimethylaluminum chloride; lithium; potassium hexamethylsilazane; L-Selectride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; tribenzylphosphine; formic acid; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; toluene; acetonitrile; xylene; 1.1: Luche reduction / 12.1: Luche reduction / 18.1: Eschenmoser-Claisen rearrangement;
DOI:10.1021/ja044280k