(5aS,13aβ)-11aα-(1,1-Dimethyl-2-propenyl)-6aα-hydroxy-2,3,6,6a,11,11a-hexahydro-1H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-5,13(5aH,13aH)-dione

Base Information

• Chemical Name: (5aS,13aβ)-11aα-(1,1-Dimethyl-2-propenyl)-6aα-hydroxy-2,3,6,6a,11,11a-hexahydro-1H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-5,13(5aH,13aH)-dione
• CAS No.: 23454-27-5
• Molecular Formula: C₂₁H₂₅N₃O₃
• Molecular Weight: 367.448
• Mol file: 23454-27-5.mol

Synonyms:1H-Pyrrolo[1'',2'':4',5']pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-5,13(5aH,13aH)-dione,11a-(1,1-dimethyl-2-propenyl)-2,3,6,6a,11,11a-hexahydro-6a-hydroxy-,(5aS,6aR,11aS,13aS)- (9CI); 1H-Pyrrolo[1'',2'':4',5']pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-5,13(5aH,13aH)-dione,11a-(1,1-dimethyl-2-propenyl)-2,3,6,6a,11,11a-hexahydro-6a-hydroxy-, [5aS-(5aa,6ab,11ab,13aa)]-;1H-Pyrrolo[1'',2'':4',5']pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-5,13(5aH,13aH)-dione,11a-(1,1-dimethylallyl)-2,3,6,6a,11,11a-hexahydro-6a-hydroxy- (8CI);Brevianamide E

Chemical Property of (5aS,13aβ)-11aα-(1,1-Dimethyl-2-propenyl)-6aα-hydroxy-2,3,6,6a,11,11a-hexahydro-1H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-5,13(5aH,13aH)-dione

Chemical Property:

• Boiling Point: 598°Cat760mmHg
• Flash Point: 315.5°C
• PSA: 72.88000
• Density: 1.36g/cm³
• LogP: 1.82750

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (5aS,13aβ)-11aα-(1,1-Dimethyl-2-propenyl)-6aα-hydroxy-2,3,6,6a,11,11a-hexahydro-1H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-5,13(5aH,13aH)-dione

There total 6 articles about (5aS,13aβ)-11aα-(1,1-Dimethyl-2-propenyl)-6aα-hydroxy-2,3,6,6a,11,11a-hexahydro-1H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-5,13(5aH,13aH)-dione 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: 70.0%

C22H29N3O4 (1350570-96-5) → brevianamide E (23454-27-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In methanol; at 80 ℃; for 96h;

DOI:10.1021/ol202880y

Reference yield:

deoxybrevianamide E (34610-68-9) → C21H25N3O3 (75557-86-7) + brevianamide E (23454-27-5)

Guidance literature:

With dimethylsulfide; oxygen; rose bengal; Yield given. Multistep reaction. Yields of byproduct given; 1.) methanol, irradiation with a 200 W halogen lamp, 3 h, -8 to -10 deg c, 2.) -10 deg C, overnight;

DOI:10.1039/P19810000959

Reference yield:

(2S)-2-amino-3-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]propanoic acid triethylamine salt (1350570-92-1) → brevianamide E (23454-27-5)

Guidance literature:

Multi-step reaction with 5 steps

1: N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide / chloroform / 2 h / 20 °C

2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 72 h / 20 °C

3: 3,3-dimethyldioxirane / dichloromethane; acetone / 3 h / -78 - 20 °C

4: 1,1,1,3',3',3'-hexafluoro-propanol / 1,2-dichloro-ethane / 2 h / 80 °C

5: N-ethyl-N,N-diisopropylamine / methanol / 96 h / 80 °C

With 1,1,1,3',3',3'-hexafluoro-propanol; 3,3-dimethyldioxirane; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In methanol; dichloromethane; chloroform; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ol202880y

upstream raw materials:

deoxybrevianamide E

(2S)-2-amino-3-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]propanoic acid triethylamine salt

(2S)-N-trityl-2-amino-3-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]propanoic acid

C₄₁H₄₃N₃O₃