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

Base Information

• Chemical Name: 1-[(benzyloxy)methyl]-3-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-indol-3-yl]-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dione
• CAS No.: 480434-53-5
• Molecular Formula: C₄₁H₃₈N₄O₁₂
• Molecular Weight: 778.772
• Mol file: 480434-53-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about 1-[(benzyloxy)methyl]-3-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-indol-3-yl]-4-(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: 6.0%

1-[(benzyloxy)methyl]-3-(1H-indol-3-yl)-4-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrole-2,5-dione (480434-40-0) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 1-[(benzyloxy)methyl]-3-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-indol-3-yl]-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dione (480434-53-5)

Guidance literature:

1-[(benzyloxy)methyl]-3-(1H-indol-3-yl)-4-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrole-2,5-dione; 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide; With silver(l) oxide; In toluene; for 3h; Heating;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h; Further stages.;

DOI:10.1021/jm0210055

Reference yield:

7-Azaindole (271-63-6) → 1-[(benzyloxy)methyl]-3-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-indol-3-yl]-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dione (480434-53-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: CH₃CH₂MgBr / tetrahydrofuran; toluene / 1.5 h / 20 °C

1.2: 57 percent / tetrahydrofuran; toluene; CH₂Cl₂ / 65 h / 40 °C

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

2.2: 75 percent / tetrahydrofuran / 4 h / 20 °C

3.1: CH₃CH₂MgBr / tetrahydrofuran; toluene / 1 h / 40 °C

3.2: 82 percent / tetrahydrofuran; toluene / 15 h / 40 °C

4.1: 37 percent / triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 15 h / 20 °C

5.1: 51 percent / n-Bu₄NF / tetrahydrofuran / 3 h / 20 °C

With ethylmagnesium bromide; tetrabutyl ammonium fluoride; sodium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; 4.1: Mitsunobu reaction;

DOI:10.1021/jm0210055

Reference yield:

indole (120-72-9) → 1-[(benzyloxy)methyl]-3-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-indol-3-yl]-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dione (480434-53-5)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 82 percent / tetrahydrofuran; toluene / 15 h / 40 °C

2.1: 37 percent / triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 15 h / 20 °C

3.1: 51 percent / n-Bu₄NF / tetrahydrofuran / 3 h / 20 °C

With ethylmagnesium bromide; tetrabutyl ammonium fluoride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; 2.1: Mitsunobu reaction;

DOI:10.1021/jm0210055

upstream raw materials:

1-[(benzyloxy)methyl]-3-(1H-indol-3-yl)-4-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrole-2,5-dione

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

indole

7-Azaindole

Downstream raw materials:

6-(benzyloxymethyl)-12-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-12,13-dihydro-5H-pyrido[3',2':4,5]pyrrolo-[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione