tert-butyl 3-((1R,2S,3S,4R,5S)-4-((2R,3R,6S)-6-((tert-butoxycarbonyl(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)amino)methyl)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-((2R,3R,4R,5R)-4-(tert-butoxycarbonyl(methyl)amino)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-2-yloxy)-5-(tert-butoxycarbonylamino)-3-hydroxycyclohexylcarbamoyl)-3-hydroxyazetidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 3-((1R,2S,3S,4R,5S)-4-((2R,3R,6S)-6-((tert-butoxycarbonyl(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)amino)methyl)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-((2R,3R,4R,5R)-4-(tert-butoxycarbonyl(methyl)amino)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-2-yloxy)-5-(tert-butoxycarbonylamino)-3-hydroxycyclohexylcarbamoyl)-3-hydroxyazetidine-1-carboxylate
• CAS No.: 1346507-95-6
• Molecular Formula: C₅₅H₉₆N₆O₂₁
• Molecular Weight: 1177.39

Synonyms:tert-butyl 3-((1R,2S,3S,4R,5S)-4-((2R,3R,6S)-6-((tert-butoxycarbonyl(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)amino)methyl)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-((2R,3R,4R,5R)-4-(tert-butoxycarbonyl(methyl)amino)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-2-yloxy)-5-(tert-butoxycarbonylamino)-3-hydroxycyclohexylcarbamoyl)-3-hydroxyazetidine-1-carboxylate

Chemical Property of tert-butyl 3-((1R,2S,3S,4R,5S)-4-((2R,3R,6S)-6-((tert-butoxycarbonyl(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)amino)methyl)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-((2R,3R,4R,5R)-4-(tert-butoxycarbonyl(methyl)amino)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-2-yloxy)-5-(tert-butoxycarbonylamino)-3-hydroxycyclohexylcarbamoyl)-3-hydroxyazetidine-1-carboxylate

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Technology Process of tert-butyl 3-((1R,2S,3S,4R,5S)-4-((2R,3R,6S)-6-((tert-butoxycarbonyl(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)amino)methyl)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-((2R,3R,4R,5R)-4-(tert-butoxycarbonyl(methyl)amino)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-2-yloxy)-5-(tert-butoxycarbonylamino)-3-hydroxycyclohexylcarbamoyl)-3-hydroxyazetidine-1-carboxylate

There total 5 articles about tert-butyl 3-((1R,2S,3S,4R,5S)-4-((2R,3R,6S)-6-((tert-butoxycarbonyl(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)amino)methyl)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-((2R,3R,4R,5R)-4-(tert-butoxycarbonyl(methyl)amino)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-2-yloxy)-5-(tert-butoxycarbonylamino)-3-hydroxycyclohexylcarbamoyl)-3-hydroxyazetidine-1-carboxylate 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: 32.0%

1-[(tert-butoxy)carbonyl]-3-hydroxyazetidine-3-carboxylic acid (1035351-06-4) + tert-butyl (2R,3R,4R,5R)-2-((1S,2R,3R,4S,6R)-6-amino-2-hydroxy-4-tert-butoxycarbonylamino-3-((2R,3R,6S)-3-tert-butoxycarbonylamino-6-((N-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)tert-butoxycarbonylamino)methyl)tetrahydro-2H-pyran-2-yloxy)cyclohexyloxy)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-4-yl(methyl)carbamate (1346507-88-7) → tert-butyl 3-((1R,2S,3S,4R,5S)-4-((2R,3R,6S)-6-((tert-butoxycarbonyl(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)amino)methyl)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-((2R,3R,4R,5R)-4-(tert-butoxycarbonyl(methyl)amino)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-2-yloxy)-5-(tert-butoxycarbonylamino)-3-hydroxycyclohexylcarbamoyl)-3-hydroxyazetidine-1-carboxylate (1346507-95-6)

Guidance literature:

1-[(tert-butoxy)carbonyl]-3-hydroxyazetidine-3-carboxylic acid; With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 - 20 ℃; for 1.5h;

tert-butyl (2R,3R,4R,5R)-2-((1S,2R,3R,4S,6R)-6-amino-2-hydroxy-4-tert-butoxycarbonylamino-3-((2R,3R,6S)-3-tert-butoxycarbonylamino-6-((N-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)tert-butoxycarbonylamino)methyl)tetrahydro-2H-pyran-2-yloxy)cyclohexyloxy)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-4-yl(methyl)carbamate; With pyridine; In tetrahydrofuran; at 20 ℃; for 18h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 3-((1R,2S,3S,4R,5S)-4-((2R,3R,6S)-6-((tert-butoxycarbonyl(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)amino)methyl)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-((2R,3R,4R,5R)-4-(tert-butoxycarbonyl(methyl)amino)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-2-yloxy)-5-(tert-butoxycarbonylamino)-3-hydroxycyclohexylcarbamoyl)-3-hydroxyazetidine-1-carboxylate (1346507-95-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / methanol / 18 h / 20 °C

2.1: hydrogen / palladium 10% on activated carbon / methanol / 18 h / 20 °C / Inert atmosphere

3.1: 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide / tetrahydrofuran / 1.5 h / 0 - 20 °C

3.2: 18 h / 20 °C

With 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; triethylamine; dicyclohexyl-carbodiimide; palladium 10% on activated carbon; In tetrahydrofuran; methanol;

Reference yield:

tert-butyl 3-oxoazetidine-1-carboxylate (398489-26-4) → tert-butyl 3-((1R,2S,3S,4R,5S)-4-((2R,3R,6S)-6-((tert-butoxycarbonyl(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)amino)methyl)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-((2R,3R,4R,5R)-4-(tert-butoxycarbonyl(methyl)amino)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-2-yloxy)-5-(tert-butoxycarbonylamino)-3-hydroxycyclohexylcarbamoyl)-3-hydroxyazetidine-1-carboxylate (1346507-95-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: zinc(II) iodide / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

1.2: 3 h / Reflux

2.1: 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide / tetrahydrofuran / 1.5 h / 0 - 20 °C

2.2: 18 h / 20 °C

With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; zinc(II) iodide; In tetrahydrofuran;

upstream raw materials:

di-tert-butyl dicarbonate

tert-butyl 3-oxoazetidine-1-carboxylate

1-[(tert-butoxy)carbonyl]-3-hydroxyazetidine-3-carboxylic acid

tert-butyl (2R,3R,4R,5R)-2-((1S,2R,3R,4S,6R)-6-amino-2-hydroxy-4-tert-butoxycarbonylamino-3-((2R,3R,6S)-3-tert-butoxycarbonylamino-6-((N-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)tert-butoxycarbonylamino)methyl)tetrahydro-2H-pyran-2-yloxy)cyclohexyloxy)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-4-yl(methyl)carbamate

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