N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N²-(tert-butyloxycarbonyl)asparaginyl-leucyl-phenylalanin-allylester

Base Information

• Chemical Name: N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N²-(tert-butyloxycarbonyl)asparaginyl-leucyl-phenylalanin-allylester
• CAS No.: 88224-29-7
• Molecular Formula: C₄₁H₅₉N₅O₁₅
• Molecular Weight: 861.944

Synonyms:N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N²-(tert-butyloxycarbonyl)asparaginyl-leucyl-phenylalanin-allylester

Chemical Property of N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N²-(tert-butyloxycarbonyl)asparaginyl-leucyl-phenylalanin-allylester

Chemical Property:

Purity/Quality:

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Technology Process of N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N²-(tert-butyloxycarbonyl)asparaginyl-leucyl-phenylalanin-allylester

There total 10 articles about N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N²-(tert-butyloxycarbonyl)asparaginyl-leucyl-phenylalanin-allylester 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: 83.0%

L-Leucyl-L-phenylalanin-allylester-hydrochlorid (88224-21-9) + N-<2-(acetylamino)-2-deoxy-3,4,6-triacetyl-β-D-glucopyranosyl>-N2-<(1,1-dimethylethoxy)carbonyl>-L-asparagine (76521-35-2) → N4-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N2-(tert-butyloxycarbonyl)asparaginyl-leucyl-phenylalanin-allylester (88224-29-7)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In dichloromethane; Ambient temperature;

DOI:10.1016/0008-6215(90)84107-6

Reference yield:

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine (4515-24-6) → N4-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N2-(tert-butyloxycarbonyl)asparaginyl-leucyl-phenylalanin-allylester (88224-29-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / EEDQ / CH₂Cl₂ / 36 h / Ambient temperature

2: 91 percent / (PPh₃)3RhCl / ethanol; H₂O / 2 h / 70 °C

3: 83 percent / triethylamine, EEDQ / CH₂Cl₂ / 72 h / Ambient temperature

With Wilkinson's catalyst; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In ethanol; dichloromethane; water;

Reference yield:

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) → N4-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N2-(tert-butyloxycarbonyl)asparaginyl-leucyl-phenylalanin-allylester (88224-29-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / triethylamine, EEDQ / CH₂Cl₂ / 12 h / Ambient temperature

2: 85 percent / HCl / diethyl ether / 2 h / Ambient temperature

3: 83 percent / triethylamine, EEDQ / CH₂Cl₂ / 72 h / Ambient temperature

With hydrogenchloride; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In diethyl ether; dichloromethane;

upstream raw materials:

L-Leucyl-L-phenylalanin-allylester-hydrochlorid

N-<2-(acetylamino)-2-deoxy-3,4,6-triacetyl-β-D-glucopyranosyl>-N²-<(1,1-dimethylethoxy)carbonyl>-L-asparagine

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine

N-tert-butoxycarbonyl-L-leucine

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