(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

Base Information

Chemical Name:(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
CAS No.:1610027-11-6
Molecular Formula:C₃₂H₃₀N₂O₆
Molecular Weight:538.6
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 10 articles about (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 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: 77.0%

: C₃₂H₃₀N₂O₆

: 1610027-11-6
(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

Guidance literature:: C₃₂H₃₀N₂O₆; With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 23 ℃; for 16h; Inert atmosphere;

With potassium carbonate; In tetrahydrofuran; methanol; at 23 ℃; for 0.5h; Inert atmosphere;
DOI:10.1002/chem.201500918

Reference yield:

: 1610027-07-0
((1S,2S,4S)-2-(benzyloxy)-7-oxabicyclo[2.2.1]hept-5-en-2-yl)methanol

: 1610027-11-6
(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

Guidance literature:: Multi-step reaction with 4 steps

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

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 48 h / -70 - 0 °C / Inert atmosphere

3: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

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

With 2,6-dimethylpyridine; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; 1: |Swern Oxidation;
DOI:10.1021/ol500990f

Reference yield:

: 1610027-05-8
((1S,2R,4S)-2-bromo-7-oxabicyclo[2.2.1]hept-5-en-2-yl)methanol

: 1610027-11-6
(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

Guidance literature:: Multi-step reaction with 6 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

With 2,6-dimethylpyridine; oxalyl dichloride; 18-crown-6 ether; camphor-10-sulfonic acid; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 3.1: |Swern Oxidation;
DOI:10.1021/ol500990f