5-benzyl-(5aR,6aR,11bS,11cS)-bis(2-azidoethyl)-7-methyl-5,5a,6a,7-tetrahydrofuro[2,3-b:5,4-b']diindole

Base Information

Chemical Name:5-benzyl-(5aR,6aR,11bS,11cS)-bis(2-azidoethyl)-7-methyl-5,5a,6a,7-tetrahydrofuro[2,3-b:5,4-b']diindole
CAS No.:582315-15-9
Molecular Formula:C₂₈H₂₈N₈O
Molecular Weight:492.583
Hs Code.:

Synonyms:5-benzyl-(5aR,6aR,11bS,11cS)-bis(2-azidoethyl)-7-methyl-5,5a,6a,7-tetrahydrofuro[2,3-b:5,4-b']diindole

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Chemical Property of 5-benzyl-(5aR,6aR,11bS,11cS)-bis(2-azidoethyl)-7-methyl-5,5a,6a,7-tetrahydrofuro[2,3-b:5,4-b']diindole

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Technology Process of 5-benzyl-(5aR,6aR,11bS,11cS)-bis(2-azidoethyl)-7-methyl-5,5a,6a,7-tetrahydrofuro[2,3-b:5,4-b']diindole

There total 11 articles about 5-benzyl-(5aR,6aR,11bS,11cS)-bis(2-azidoethyl)-7-methyl-5,5a,6a,7-tetrahydrofuro[2,3-b:5,4-b']diindole 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:

: 1217-89-6
1-benzylisatin

: 582315-15-9
5-benzyl-(5aR,6aR,11bS,11cS)-bis(2-azidoethyl)-7-methyl-5,5a,6a,7-tetrahydrofuro[2,3-b:5,4-b']diindole

Guidance literature:: Multi-step reaction with 8 steps

1.1: 76 percent / AcOH; HCl / 6 h / 110 °C

2.1: 97 percent / Cs₂CO₃ / dimethylformamide / 24 h / 20 °C

3.1: 88 percent / H₂ / PtO₂ / ethyl acetate / 20 °C / 760 Torr

4.1: LHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -40 °C

4.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 13 h / -35 - 20 °C

5.1: 98 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 3 h / 20 °C

6.1: NaIO₄ / H₂O; tetrahydrofuran / 12 h / 20 °C

6.2: 87 percent / NaBH₄ / methanol / 0.17 h / 20 °C

7.1: Red-Al(R) / tetrahydrofuran / 1.5 h / 67 °C

8.1: 3.27 g / PPh₃; HN₃; DEAD / 0 - 20 °C / pH 13

With hydrogenchloride; sodium periodate; tris-(2-chloro-ethyl)-amine; camphor-10-sulfonic acid; hydrogen; caesium carbonate; acetic acid; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium hexamethyldisilazane; diethylazodicarboxylate; platinum(IV) oxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 8.1: Mitsunobu reaction;
DOI:10.1016/S0040-4020(03)00855-X

Reference yield:

: 91-56-5,1186480-61-4,84788-92-1
indole-2,3-dione

: 582315-15-9
5-benzyl-(5aR,6aR,11bS,11cS)-bis(2-azidoethyl)-7-methyl-5,5a,6a,7-tetrahydrofuro[2,3-b:5,4-b']diindole

Guidance literature:: Multi-step reaction with 9 steps

1.1: 99 percent / NaH / dimethylformamide / 0.25 h

2.1: 76 percent / AcOH; HCl / 6 h / 110 °C

3.1: 97 percent / Cs₂CO₃ / dimethylformamide / 24 h / 20 °C

4.1: 88 percent / H₂ / PtO₂ / ethyl acetate / 20 °C / 760 Torr

5.1: LHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -40 °C

5.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 13 h / -35 - 20 °C

6.1: 98 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 3 h / 20 °C

7.1: NaIO₄ / H₂O; tetrahydrofuran / 12 h / 20 °C

7.2: 87 percent / NaBH₄ / methanol / 0.17 h / 20 °C

8.1: Red-Al(R) / tetrahydrofuran / 1.5 h / 67 °C

9.1: 3.27 g / PPh₃; HN₃; DEAD / 0 - 20 °C / pH 13

With hydrogenchloride; sodium periodate; tris-(2-chloro-ethyl)-amine; camphor-10-sulfonic acid; hydrogen; sodium hydride; caesium carbonate; acetic acid; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium hexamethyldisilazane; diethylazodicarboxylate; platinum(IV) oxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 9.1: Mitsunobu reaction;
DOI:10.1016/S0040-4020(03)00855-X

Reference yield:

: 100-39-0
benzyl bromide

: 582315-15-9
5-benzyl-(5aR,6aR,11bS,11cS)-bis(2-azidoethyl)-7-methyl-5,5a,6a,7-tetrahydrofuro[2,3-b:5,4-b']diindole

Guidance literature:: Multi-step reaction with 9 steps

1.1: 99 percent / NaH / dimethylformamide / 0.25 h

2.1: 76 percent / AcOH; HCl / 6 h / 110 °C

3.1: 97 percent / Cs₂CO₃ / dimethylformamide / 24 h / 20 °C

4.1: 88 percent / H₂ / PtO₂ / ethyl acetate / 20 °C / 760 Torr

5.1: LHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -40 °C

5.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 13 h / -35 - 20 °C

6.1: 98 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 3 h / 20 °C

7.1: NaIO₄ / H₂O; tetrahydrofuran / 12 h / 20 °C

7.2: 87 percent / NaBH₄ / methanol / 0.17 h / 20 °C

8.1: Red-Al(R) / tetrahydrofuran / 1.5 h / 67 °C

9.1: 3.27 g / PPh₃; HN₃; DEAD / 0 - 20 °C / pH 13

With hydrogenchloride; sodium periodate; tris-(2-chloro-ethyl)-amine; camphor-10-sulfonic acid; hydrogen; sodium hydride; caesium carbonate; acetic acid; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium hexamethyldisilazane; diethylazodicarboxylate; platinum(IV) oxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 9.1: Mitsunobu reaction;
DOI:10.1016/S0040-4020(03)00855-X