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

Base Information

• Chemical Name: 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
• CAS No.: 797761-57-0
• Molecular Formula: C₅₂H₈₄N₆O₂₇
• Molecular Weight: 1225.26

Synonyms: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

Chemical Property of 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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Technology Process of 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

There total 5 articles about 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 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%

uridine 5'-diphospho-D-galactose (2956-16-3) + 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) → N-{3-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]propyl}-Nα-{8-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]-5-aza-1,4-dioxooctyl}-Nε-(benzyloxycarbonyl)-L-lysinamide (797761-57-0)

Guidance literature:

With β-1,4-galactosyltransferase; manganese(ll) chloride; In various solvent(s); at 37 ℃; for 48h; pH=6.0;

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-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]propyl}-Nα-{8-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]-5-aza-1,4-dioxooctyl}-Nε-(benzyloxycarbonyl)-L-lysinamide (797761-57-0)

Guidance literature:

Multi-step reaction with 5 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

5: 83 percent / β-1,4-galactosyltransferase; MnCl2 / various solvent(s) / 48 h / 37 °C / pH 6.0

With pyridine; β-1,4-galactosyltransferase; triethylamine; N-ethyl-N,N-diisopropylamine; manganese(ll) chloride; 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-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]propyl}-Nα-{8-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]-5-aza-1,4-dioxooctyl}-Nε-(benzyloxycarbonyl)-L-lysinamide (797761-57-0)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 83 percent / β-1,4-galactosyltransferase; MnCl2 / various solvent(s) / 48 h / 37 °C / pH 6.0

With β-1,4-galactosyltransferase; triethylamine; N-ethyl-N,N-diisopropylamine; manganese(ll) chloride; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja046426l

upstream raw materials:

uridine 5'-diphospho-D-galactose

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

N₆-[(benzyloxy)carbonyl]-L-lysine

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

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