N-((1R,2R,3S,4S,5S)-4-((3-acetylphenyl)amino)-5-azido-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methylcyclopentyl)pyrrolidine-1-carboxamide

Base Information

Chemical Name:N-((1R,2R,3S,4S,5S)-4-((3-acetylphenyl)amino)-5-azido-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methylcyclopentyl)pyrrolidine-1-carboxamide
CAS No.:1428762-90-6
Molecular Formula:C₂₂H₃₂N₆O₆
Molecular Weight:476.533
Hs Code.:

N-((1R,2R,3S,4S,5S)-4-((3-acetylphenyl)amino)-5-azido-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methylcyclopentyl)pyrrolidine-1-carboxamide

Synonyms:N-((1R,2R,3S,4S,5S)-4-((3-acetylphenyl)amino)-5-azido-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methylcyclopentyl)pyrrolidine-1-carboxamide

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Chemical Property of N-((1R,2R,3S,4S,5S)-4-((3-acetylphenyl)amino)-5-azido-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methylcyclopentyl)pyrrolidine-1-carboxamide

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Technology Process of N-((1R,2R,3S,4S,5S)-4-((3-acetylphenyl)amino)-5-azido-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methylcyclopentyl)pyrrolidine-1-carboxamide

There total 5 articles about N-((1R,2R,3S,4S,5S)-4-((3-acetylphenyl)amino)-5-azido-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methylcyclopentyl)pyrrolidine-1-carboxamide 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: 87.0%

: 1428762-86-0
N-((5S,6R,7R,8S,9S)-9-((3-acetylphenyl)amino)-8-azido-6-hydroxy-7-((S)-1-hydroxyethyl)-2,2,6-trimethyl-1,3-dioxaspiro[4.4]nonan-7-yl)pyrrolidine-1-carboxamide

: 1428762-90-6
N-((1R,2R,3S,4S,5S)-4-((3-acetylphenyl)amino)-5-azido-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methylcyclopentyl)pyrrolidine-1-carboxamide

Guidance literature:: N-((5S,6R,7R,8S,9S)-9-((3-acetylphenyl)amino)-8-azido-6-hydroxy-7-((S)-1-hydroxyethyl)-2,2,6-trimethyl-1,3-dioxaspiro[4.4]nonan-7-yl)pyrrolidine-1-carboxamide; With trifluoroacetic acid; In water; acetonitrile; at 20 ℃; for 0.75h;

With sodium hydrogencarbonate; In water; acetonitrile; at 0 ℃;
DOI:10.1016/j.bmc.2013.01.037

Reference yield:

: 1428762-78-0
(S)-1-((5S,6R,7R,8S,9S)-8-azido-6-hydroxy-2,2,6-trimethyl-9-((3-(prop-1-en-2-yl)phenyl)amino)-7-(pyrrolidine-1-carboxamido)-1,3-dioxaspiro[4.4]nonan-7-yl)ethyl 4-methoxybenzoate

: 1428762-90-6
N-((1R,2R,3S,4S,5S)-4-((3-acetylphenyl)amino)-5-azido-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methylcyclopentyl)pyrrolidine-1-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; acetone; water / 2 h / 20 °C

2.2: 0.5 h / 20 °C

3.1: sodium periodate / tetrahydrofuran; water / 3 h / 20 °C

4.1: trifluoroacetic acid / water; acetonitrile / 0.75 h / 20 °C

4.2: 0 °C

With sodium periodate; osmium(VIII) oxide; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetone; toluene; acetonitrile;
DOI:10.1016/j.bmc.2013.01.037

Reference yield:

: 1295471-62-3
C₃₀H₃₅N₅O₇

: 1428762-90-6
N-((1R,2R,3S,4S,5S)-4-((3-acetylphenyl)amino)-5-azido-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methylcyclopentyl)pyrrolidine-1-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 0 - 20 °C

2.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; acetone; water / 2 h / 20 °C

3.2: 0.5 h / 20 °C

4.1: sodium periodate / tetrahydrofuran; water / 3 h / 20 °C

5.1: trifluoroacetic acid / water; acetonitrile / 0.75 h / 20 °C

5.2: 0 °C

With sodium periodate; osmium(VIII) oxide; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetone; toluene; acetonitrile;
DOI:10.1016/j.bmc.2013.01.037