1-(6-amino-6-deoxy-β-D-glucopyranosyl)-4-chloro-3-(4-cyclopropylbenzyl)-1H-indole

Base Information

• Chemical Name: 1-(6-amino-6-deoxy-β-D-glucopyranosyl)-4-chloro-3-(4-cyclopropylbenzyl)-1H-indole
• CAS No.: 1443333-08-1
• Molecular Formula: C₂₄H₂₇ClN₂O₄
• Molecular Weight: 442.942

Synonyms:1-(6-amino-6-deoxy-β-D-glucopyranosyl)-4-chloro-3-(4-cyclopropylbenzyl)-1H-indole

Chemical Property of 1-(6-amino-6-deoxy-β-D-glucopyranosyl)-4-chloro-3-(4-cyclopropylbenzyl)-1H-indole

Chemical Property:

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Technology Process of 1-(6-amino-6-deoxy-β-D-glucopyranosyl)-4-chloro-3-(4-cyclopropylbenzyl)-1H-indole

There total 4 articles about 1-(6-amino-6-deoxy-β-D-glucopyranosyl)-4-chloro-3-(4-cyclopropylbenzyl)-1H-indole 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: 91.0%

1-(6-azido-6-deoxy-β-D-glucopyranosyl)-4-chloro-3-(4-cyclopropylbenzyl)-1H-indole (1443333-03-6) → 1-(6-amino-6-deoxy-β-D-glucopyranosyl)-4-chloro-3-(4-cyclopropylbenzyl)-1H-indole (1443333-08-1)

Guidance literature:

With acetic acid; zinc; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2016.03.058

Reference yield:

N-indolylglucoside 4-chloro-3-(4-cyclopropylbenzyl)-1-(β-D-glucopyranosyl)-1H-indole → 1-(6-amino-6-deoxy-β-D-glucopyranosyl)-4-chloro-3-(4-cyclopropylbenzyl)-1H-indole (1443333-08-1)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 3 h / 0 - 20 °C / Inert atmosphere

2: sodium azide / N,N-dimethyl-formamide / 80 °C

3: acetic acid; zinc / tetrahydrofuran / 20 °C / Inert atmosphere

With pyridine; sodium azide; acetic acid; zinc; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2016.03.058

Reference yield:

C25H28ClNO7S → 1-(6-amino-6-deoxy-β-D-glucopyranosyl)-4-chloro-3-(4-cyclopropylbenzyl)-1H-indole (1443333-08-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium azide / N,N-dimethyl-formamide / 80 °C

2: acetic acid; zinc / tetrahydrofuran / 20 °C / Inert atmosphere

With sodium azide; acetic acid; zinc; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2016.03.058

upstream raw materials:

1-(6-azido-6-deoxy-β-D-glucopyranosyl)-4-chloro-3-(4-cyclopropylbenzyl)-1H-indole

Downstream raw materials:

(1‐[6‐(acetylamino)‐6‐deoxy‐β‐D‐glucopyranosyl]‐4‐chloro‐3‐(4‐cyclopropylbenzyl)‐1H‐indole)

4-chloro-1-{6-[(chloroacetyl)amino]-6-deoxy-β-D-glucopyranosyl}-3-(4-cyclopropylbenzyl)-1H-indole

4-chloro-3-(4-cyclopropylbenzyl)-1-{6-deoxy-6-[(dichloroacetyl)amino]-β-D-glucopyranosyl}-1H-indole

4-chloro-1-{6-[(3-chloropropanoyl)amino]-6-deoxy-β-D-glucopyranosyl}-3-(4-cyclopropylbenzyl)-1H-indole

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