N-[3-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)propyl]-N^α-[8-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)-5-aza-1,4-dioxooctyl]-N^ε-(benzyloxycarbonyl)-L-lysinamide

Base Information

• Chemical Name: N-[3-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)propyl]-N^α-[8-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)-5-aza-1,4-dioxooctyl]-N^ε-(benzyloxycarbonyl)-L-lysinamide
• CAS No.: 797761-56-9
• Molecular Formula: C₄₀H₆₄N₆O₁₇
• Molecular Weight: 900.978

Synonyms:N-[3-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)propyl]-N^α-[8-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)-5-aza-1,4-dioxooctyl]-N^ε-(benzyloxycarbonyl)-L-lysinamide

Chemical Property of N-[3-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)propyl]-N^α-[8-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)-5-aza-1,4-dioxooctyl]-N^ε-(benzyloxycarbonyl)-L-lysinamide

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

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Technology Process of N-[3-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)propyl]-N^α-[8-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)-5-aza-1,4-dioxooctyl]-N^ε-(benzyloxycarbonyl)-L-lysinamide

There total 5 articles about N-[3-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)propyl]-N^α-[8-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)-5-aza-1,4-dioxooctyl]-N^ε-(benzyloxycarbonyl)-L-lysinamide 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: 90.0%

N-[3-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxyl)propyl]-Nα-[8-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxyl)-5-aza-1,4-dioxooctyl]-Nε-(benzyloxycarbonyl)-L-lysinamide (797761-55-8) → N-[3-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)propyl]-Nα-[8-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)-5-aza-1,4-dioxooctyl]-Nε-(benzyloxycarbonyl)-L-lysinamide (797761-56-9)

Guidance literature:

With triethylamine; In methanol; at 20 ℃; for 4h;

DOI:10.1021/ja046426l

Reference yield:

N6-[(benzyloxy)carbonyl]-L-lysine (1155-64-2,57705-97-2,67178-46-5,25931-47-9) → N-[3-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)propyl]-Nα-[8-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)-5-aza-1,4-dioxooctyl]-Nε-(benzyloxycarbonyl)-L-lysinamide (797761-56-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / methanol / 12 h / 40 °C

2: 77 percent / pyridine / dimethylformamide / 1 h / 20 °C

3: 84 percent / iPr₂NEt / dimethylformamide / 17 h / 20 °C

4: 90 percent / aq. Et₃N / methanol / 4 h / 20 °C

With pyridine; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja046426l

Reference yield:

3-aminopropyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside → N-[3-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)propyl]-Nα-[8-(2-acetamido-2-deoxy-β-D-glucopyranosyloxyl)-5-aza-1,4-dioxooctyl]-Nε-(benzyloxycarbonyl)-L-lysinamide (797761-56-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / iPr₂NEt / dimethylformamide / 17 h / 20 °C

2: 90 percent / aq. Et₃N / methanol / 4 h / 20 °C

With triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja046426l

upstream raw materials:

N-[3-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxyl)propyl]-N^α-[8-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxyl)-5-aza-1,4-dioxooctyl]-N^ε-(benzyloxycarbonyl)-L-lysinamide

N₆-[(benzyloxy)carbonyl]-L-lysine

N^α-(3-carboxy-1-oxopropyl)-N^ε-(benzyloxycarbonyl)-L-lysine

N^α-(3-carboxy-1-oxopropyl)-N^ε-(benzyloxycarbonyl)-L-lysine bis(pentafluorophenyl) ester

Downstream raw materials:

N-{3-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]propyl}-N^α-{8-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]-5-aza-1,4-dioxooctyl}-N^ε-(benzyloxycarbonyl)-L-lysinamide

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