tert-butyl (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-6-((S)-5-(1,3-dioxoisoindolin-2-yl)-2-hydroxypentanamido)-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

Base Information

• Chemical Name: tert-butyl (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-6-((S)-5-(1,3-dioxoisoindolin-2-yl)-2-hydroxypentanamido)-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
• CAS No.: 1346507-89-8
• Molecular Formula: C₅₉H₉₄N₆O₂₁
• Molecular Weight: 1223.42

Synonyms:tert-butyl (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-6-((S)-5-(1,3-dioxoisoindolin-2-yl)-2-hydroxypentanamido)-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

Chemical Property of tert-butyl (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-6-((S)-5-(1,3-dioxoisoindolin-2-yl)-2-hydroxypentanamido)-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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of tert-butyl (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-6-((S)-5-(1,3-dioxoisoindolin-2-yl)-2-hydroxypentanamido)-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

There total 7 articles about tert-butyl (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-6-((S)-5-(1,3-dioxoisoindolin-2-yl)-2-hydroxypentanamido)-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 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: 73.0%

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) + (S)-5-(1,3-dioxoisoindolin-2-yl)-2-hydroxypentanoic acid → tert-butyl (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-6-((S)-5-(1,3-dioxoisoindolin-2-yl)-2-hydroxypentanamido)-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 (1346507-89-8)

Guidance literature:

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 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 - 20 ℃; for 1.5h;

(S)-5-(1,3-dioxoisoindolin-2-yl)-2-hydroxypentanoic acid; With pyridine; In tetrahydrofuran; at 20 ℃; for 18h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-6-((S)-5-(1,3-dioxoisoindolin-2-yl)-2-hydroxypentanamido)-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 (1346507-89-8)

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:

Boc-Orn(Z)-OH (2480-93-5) → tert-butyl (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-6-((S)-5-(1,3-dioxoisoindolin-2-yl)-2-hydroxypentanamido)-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 (1346507-89-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogen / palladium 10% on activated carbon / methanol / 18 h / 20 °C / 760.05 Torr / Inert atmosphere

2.1: N,N-dimethyl-formamide / 24 h / 120 °C / Sealed tube

3.1: trifluoroacetic acid / 1,2-dichloro-ethane / 2 h / 0 - 20 °C

3.2: 18 h / 20 °C

3.3: pH 1

4.1: 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide / tetrahydrofuran / 1.5 h / 0 - 20 °C

4.2: 18 h / 20 °C

With 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium 10% on activated carbon; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

upstream raw materials:

di-tert-butyl dicarbonate

Boc-Orn(Z)-OH

N₂-(tert-butoxycarbonyl)-L-ornithine

N^α-(tert-butyloxycarbonyl)-N^δ-phthalimido-L-ornithine

Downstream raw materials:

tert-butyl (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-6-((S)-5-amino-2-hydroxypentanamido)-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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