(2R,4aR,6aR,7aR,9R,11aR,13aR,14aR)-7a,14a-dihydroxy-6,13-dioxooctadecahydropyrazino[1,2-a:4,5-a']diindole-2,9-diyl dibenzoate

Base Information

• Chemical Name: (2R,4aR,6aR,7aR,9R,11aR,13aR,14aR)-7a,14a-dihydroxy-6,13-dioxooctadecahydropyrazino[1,2-a:4,5-a']diindole-2,9-diyl dibenzoate
• CAS No.: 1610027-14-9
• Molecular Formula: C₃₂H₃₄N₂O₈
• Molecular Weight: 574.631

Synonyms:

Chemical Property of (2R,4aR,6aR,7aR,9R,11aR,13aR,14aR)-7a,14a-dihydroxy-6,13-dioxooctadecahydropyrazino[1,2-a:4,5-a']diindole-2,9-diyl dibenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,6aR,7aR,9R,11aR,13aR,14aR)-7a,14a-dihydroxy-6,13-dioxooctadecahydropyrazino[1,2-a:4,5-a']diindole-2,9-diyl dibenzoate

There total 10 articles about (2R,4aR,6aR,7aR,9R,11aR,13aR,14aR)-7a,14a-dihydroxy-6,13-dioxooctadecahydropyrazino[1,2-a:4,5-a']diindole-2,9-diyl dibenzoate 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:

((1S,2R,4S)-2-bromo-7-oxabicyclo[2.2.1]hept-5-en-2-yl)methanol (1610027-05-8) → (2R,4aR,6aR,7aR,9R,11aR,13aR,14aR)-7a,14a-dihydroxy-6,13-dioxooctadecahydropyrazino[1,2-a:4,5-a']diindole-2,9-diyl dibenzoate (1610027-14-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium carbonate; 18-crown-6 ether / water; 1,4-dioxane / 20 h / Reflux

2.1: camphor-10-sulfonic acid / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

2.2: 4 h / 0 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 - -70 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 48 h / -70 - 0 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

6.1: potassium carbonate / tetrahydrofuran; methanol / 0.5 h / Inert atmosphere

7.1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

8.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / Inert atmosphere

With 2,6-dimethylpyridine; dmap; oxalyl dichloride; 18-crown-6 ether; palladium 10% on activated carbon; camphor-10-sulfonic acid; hydrogen; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; 3.1: |Swern Oxidation;

DOI:10.1021/ol500990f

Reference yield:

(1S,2S,4S)-2-(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-ol (1610027-06-9) → (2R,4aR,6aR,7aR,9R,11aR,13aR,14aR)-7a,14a-dihydroxy-6,13-dioxooctadecahydropyrazino[1,2-a:4,5-a']diindole-2,9-diyl dibenzoate (1610027-14-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: camphor-10-sulfonic acid / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

1.2: 4 h / 0 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 - -70 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 48 h / -70 - 0 °C / Inert atmosphere

4.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

5.1: potassium carbonate / tetrahydrofuran; methanol / 0.5 h / Inert atmosphere

6.1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / Inert atmosphere

With 2,6-dimethylpyridine; dmap; oxalyl dichloride; palladium 10% on activated carbon; camphor-10-sulfonic acid; hydrogen; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 2.1: |Swern Oxidation;

DOI:10.1021/ol500990f

Reference yield:

C14H14O3 → (2R,4aR,6aR,7aR,9R,11aR,13aR,14aR)-7a,14a-dihydroxy-6,13-dioxooctadecahydropyrazino[1,2-a:4,5-a']diindole-2,9-diyl dibenzoate (1610027-14-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; dimethyl sulfoxide / 48 h / -70 - 0 °C / Inert atmosphere

2: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

3: potassium carbonate / tetrahydrofuran; methanol / 0.5 h / Inert atmosphere

4: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / Inert atmosphere

With 2,6-dimethylpyridine; dmap; palladium 10% on activated carbon; hydrogen; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; 1: |Swern Oxidation;

DOI:10.1021/ol500990f

upstream raw materials:

(Z)-1-acetyl-3-(((1S,2S,4S)-2-(benzyloxy)-7-oxabicyclo[2.2.1]hept-5-en-2-yl)methylene)piperazine-2,5-dione

C₃₈H₄₆N₂O₆Si₂

(2S,4aR,7aS,9S,11aR,14aS)-7a,14a-bis(benzyloxy)-2,9-dihydroxy-1,7a,8,9,11a,14a-hexahydropyrazino[1,2-a:4,5-a']diindole-6,13(2H,4aH)-dione

(3Z,6Z)-3,6-bis(((1S,2S,4S)-2-(benzyloxy)-7-oxabicyclo[2.2.1]hept-5-en-2-yl)methylene)piperazine-2,5-dione

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