Bisdehydroneotuberostemonine

Base Information

• Chemical Name: Bisdehydroneotuberostemonine
• CAS No.: 106861-40-9
• Molecular Formula: C₂₂H₂₉NO₄
• Molecular Weight: 371.477
• Wikidata: Q105235395
• Mol file: 106861-40-9.mol

Synonyms:bisdehydro-neotubero-stemonine;bisdehydroneotuberostemonine

Chemical Property of Bisdehydroneotuberostemonine

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 371.20965841
• Heavy Atom Count: 27
• Complexity: 636

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C2CCCCN3C2=C(C=C3C4CC(C(=O)O4)C)C5C1OC(=O)C5C

Technology Process of Bisdehydroneotuberostemonine

There total 40 articles about Bisdehydroneotuberostemonine 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:

(-)-tuberostemonine (6879-01-2) → didehydrotuberostemonine (106861-40-9,160333-27-7)

Guidance literature:

With ethanol; silver(l) oxide;

Reference yield:

(2S,3aR,6S,7aR)-6-hydroxy-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (171523-46-9) → didehydrotuberostemonine (106861-40-9,160333-27-7)

Guidance literature:

Multi-step reaction with 22 steps

1.1: 97 percent / imidazole; dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

2.1: 90 percent / triethylsilane; palladium(II) acetate; triethylamine / CH₂Cl₂ / 15 h / 20 °C

3.1: 96 percent / K₂CO₃ / toluene / 15 h / 60 °C

4.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

5.1: 88 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 15 h / 20 °C

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

6.2: 66 percent / tetrahydrofuran / 0.5 h / -90 °C

7.1: 92 percent / Grubb's 2nd generation catalyst / CH₂Cl₂ / 2 h / Heating

8.1: 91 percent / triethylamine / CH₂Cl₂ / 3 h / 20 °C

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

9.2: 89 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 3.5 h / 20 °C

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

11.1: 1.0 g / imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 14 h / 20 °C

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

12.2: 94 percent / CH₂Cl₂; hexane / 14 h / 20 °C

13.1: 4,4'-di-tert-butylbiphenyl; lithium / tetrahydrofuran / 0.5 h / -78 °C

13.2: 95 percent / tetrahydrofuran / 0.25 h / -78 °C

14.1: 80 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 17 h / -78 - -15 °C

15.1: 388 mg / p-toluenesulfonic acid monohydrate / methanol / 20 h / 20 °C

16.1: 65 percent / xylene / 19 h / 130 - 140 °C

17.1: 81 percent / acetonitrile; H₂O / 18 h / 0 °C

18.1: 27 percent / AIBN; α,α,α-trifluorotoluene / 95 °C

19.1: 85 percent / Grubb's 2nd generation catalyst; allyltritylamine; N,N-diisopropylethylamine / CH₂Cl₂ / 16 h / Heating

20.1: p-toluenesulfonic acid monohydrate / CH₂Cl₂ / 0.5 h / Heating

20.2: 81 percent / Grubb's 2nd generation catalyst / CH₂Cl₂ / 60 h / Heating

21.1: 97 percent / H₂ / Pd/C / methanol / 17 h / 20 °C

22.1: Ag₂O / acetone / 15 h / 40 °C

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; triethylsilane; dmap; sodium tetrahydroborate; Wilkinson's catalyst; cerium(III) chloride; tetrapropylammonium perruthennate; 2,2'-azobis(isobutyronitrile); α,α,α-trifluorotoluene; 4,4'-di-tert-butylbiphenyl; N-tritylprop-2-en-1-amine; tetrabutyl ammonium fluoride; hydrogen; palladium diacetate; dimethylaluminum chloride; lithium; potassium hexamethylsilazane; L-Selectride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; silver(l) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetone; toluene; acetonitrile; xylene; 10.1: Luche reduction / 16.1: Eschenmoser-Claisen rearrangement;

DOI:10.1021/ja044280k

Reference yield:

(2S,3aR,7aR)-3a-hydroxy-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (144534-49-6) → didehydrotuberostemonine (106861-40-9,160333-27-7)

Guidance literature:

Multi-step reaction with 25 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

21.1: 27 percent / AIBN; α,α,α-trifluorotoluene / 95 °C

22.1: 85 percent / Grubb's 2nd generation catalyst; allyltritylamine; N,N-diisopropylethylamine / CH₂Cl₂ / 16 h / Heating

23.1: p-toluenesulfonic acid monohydrate / CH₂Cl₂ / 0.5 h / Heating

23.2: 81 percent / Grubb's 2nd generation catalyst / CH₂Cl₂ / 60 h / Heating

24.1: 97 percent / H₂ / Pd/C / methanol / 17 h / 20 °C

25.1: Ag₂O / acetone / 15 h / 40 °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; 2,2'-azobis(isobutyronitrile); α,α,α-trifluorotoluene; 4,4'-di-tert-butylbiphenyl; N-tritylprop-2-en-1-amine; tetrabutyl ammonium fluoride; hydrogen; palladium diacetate; dimethylaluminum chloride; lithium; potassium hexamethylsilazane; L-Selectride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; tribenzylphosphine; silver(l) oxide; palladium on activated charcoal; formic acid; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetone; toluene; acetonitrile; xylene; 2.1: Luche reduction / 13.1: Luche reduction / 19.1: Eschenmoser-Claisen rearrangement;

DOI:10.1021/ja044280k

upstream raw materials:

(-)-tuberostemonine

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

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

<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

Refernces

• 1、 Wipf, Peter,Spencer, Stacey R.. "Asymmetric total syntheses of tuberostemonine, didehydrotuberostemonine, and 13-epituberostemonine". . p. 225 - 235. Retrieved 2007/10/03.