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

Base Information

• Chemical Name: 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
• CAS No.: 1346507-90-1
• Molecular Formula: C₅₁H₉₂N₆O₁₉
• Molecular Weight: 1093.32

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 9 articles about 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 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: 44.0%

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) → 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 (1346507-90-1)

Guidance literature:

With ethanol; hydrazine; for 1.5h; Reflux;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 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 (1346507-90-1)

Guidance literature:

Multi-step reaction with 4 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

4.1: ethanol; hydrazine / 1.5 h / Reflux

With 1-hydroxy-pyrrolidine-2,5-dione; ethanol; hydrogen; triethylamine; dicyclohexyl-carbodiimide; hydrazine; 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-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 (1346507-90-1)

Guidance literature:

Multi-step reaction with 5 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

5.1: ethanol; hydrazine / 1.5 h / Reflux

With 1-hydroxy-pyrrolidine-2,5-dione; ethanol; hydrogen; dicyclohexyl-carbodiimide; trifluoroacetic acid; hydrazine; 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

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