1-[(benzyloxy)methyl]-3-[1H-indol-3-yl]-4-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrole-2,5-dione

Base Information

Chemical Name:1-[(benzyloxy)methyl]-3-[1H-indol-3-yl]-4-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrole-2,5-dione
CAS No.:480434-46-6
Molecular Formula:C₄₁H₃₈N₄O₁₂
Molecular Weight:778.772
Hs Code.:

Synonyms:1-[(benzyloxy)methyl]-3-[1H-indol-3-yl]-4-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrole-2,5-dione

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Chemical Property of 1-[(benzyloxy)methyl]-3-[1H-indol-3-yl]-4-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrole-2,5-dione

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Technology Process of 1-[(benzyloxy)methyl]-3-[1H-indol-3-yl]-4-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrole-2,5-dione

There total 6 articles about 1-[(benzyloxy)methyl]-3-[1H-indol-3-yl]-4-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrole-2,5-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: 72.0%

: 480434-45-5
1-[(benzyloxy)methyl]-3-[1-(phenylsulfonyl)-1H-indol-3-yl]-4-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrole-2,5-dione

: 480434-46-6
1-[(benzyloxy)methyl]-3-[1H-indol-3-yl]-4-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrole-2,5-dione

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2.5h;
DOI:10.1021/jm0210055

Reference yield:

: 120-72-9
indole

: 480434-46-6
1-[(benzyloxy)methyl]-3-[1H-indol-3-yl]-4-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrole-2,5-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: CH₃CH₂MgBr / tetrahydrofuran / 1 h / 40 °C

1.2: 75 percent / tetrahydrofuran / 15 h / 20 °C

2.1: NaH / tetrahydrofuran / 1 h / 0 °C

2.2: 50 percent / tetrahydrofuran / 4 h / 20 °C

3.1: LiHMDS / toluene; hexane / 1 h / -15 °C

3.2: 46 percent / toluene; hexane / 24 h / 20 °C

4.1: 61 percent / triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 15 h / 20 °C

5.1: 72 percent / n-Bu₄NF / tetrahydrofuran / 2.5 h / 20 °C

With ethylmagnesium bromide; tetrabutyl ammonium fluoride; sodium hydride; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; hexane; toluene; 4.1: Mitsunobu reaction;
DOI:10.1021/jm0210055

Reference yield:

: 102147-52-4
N-benzyloxymethyl-3,4-dibromomaleimide

: 480434-46-6
1-[(benzyloxy)methyl]-3-[1H-indol-3-yl]-4-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrole-2,5-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: CH₃CH₂MgBr / tetrahydrofuran / 1 h / 40 °C

1.2: 75 percent / tetrahydrofuran / 15 h / 20 °C

2.1: NaH / tetrahydrofuran / 1 h / 0 °C

2.2: 50 percent / tetrahydrofuran / 4 h / 20 °C

3.1: LiHMDS / toluene; hexane / 1 h / -15 °C

3.2: 46 percent / toluene; hexane / 24 h / 20 °C

4.1: 61 percent / triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 15 h / 20 °C

5.1: 72 percent / n-Bu₄NF / tetrahydrofuran / 2.5 h / 20 °C

With ethylmagnesium bromide; tetrabutyl ammonium fluoride; sodium hydride; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; hexane; toluene; 4.1: Mitsunobu reaction;
DOI:10.1021/jm0210055