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

Base Information

Chemical Name: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
CAS No.:480434-45-5
Molecular Formula:C₄₇H₄₂N₄O₁₄S
Molecular Weight:918.935
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 6 articles about 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 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: 61.0%

: 3947-62-4,10343-06-3,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,6207-76-7
2,3,4,6-tetraacetylglucose

: 480434-37-5
1-[(benzyloxy)methyl]-3-[1-(phenylsulfonyl)-1H-indol-3-yl]-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dione

: 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

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 15h;
DOI:10.1021/jm0210055

Reference yield:

: 3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3
2,3,4,5-tetra-O-acetyl-D-glucopyranose

: 480434-37-5
1-[(benzyloxy)methyl]-3-[1-(phenylsulfonyl)-1H-indol-3-yl]-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dione

: C₄₇H₄₂N₄O₁₄S

: 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

Guidance literature:: 2,3,4,5-tetra-O-acetyl-D-glucopyranose; 1-[(benzyloxy)methyl]-3-[1-(phenylsulfonyl)-1H-indol-3-yl]-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dione; With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at -78 - 20 ℃; for 15h;

With water; In tetrahydrofuran;

Reference yield:

: 120-72-9
indole

: 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

Guidance literature:: Multi-step reaction with 4 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

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