N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-asparagin-benzylester

Base Information

• Chemical Name: N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-asparagin-benzylester
• CAS No.: 79134-90-0
• Molecular Formula: C₂₅H₃₃N₃O₁₁
• Molecular Weight: 551.551

Synonyms:N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-asparagin-benzylester

Chemical Property of N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-asparagin-benzylester

Chemical Property:

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Technology Process of N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-asparagin-benzylester

There total 4 articles about N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-asparagin-benzylester 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: 68.0%

N4-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N2-<2-(triphenylphosphonio)ethoxycarbonyl>asparagin-benzylester-chlorid (86088-21-3) → N4-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-asparagin-benzylester (79134-90-0)

Guidance literature:

With diethylamine; In tert-butyl alcohol; for 0.5h; Ambient temperature;

DOI:10.1002/jlac.198319830302

Reference yield: 67.0%

{2-[(S)-1-Benzyloxycarbonyl-2-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylcarbamoyl)-ethylcarbamoyloxy]-ethyl}-triphenyl-phosphonium (79134-88-6) → N4-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-asparagin-benzylester (79134-90-0)

Guidance literature:

With diethylamine; In tert-butyl alcohol; for 0.5h; Ambient temperature;

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)-asparagin-benzylester (79134-90-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / EEDQ / CHCl₃ / -10 deg C to RT in 12h

2: 67 percent / 20percent HNEt₂ / 2-methyl-propan-2-ol / 0.5 h / Ambient temperature

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; diethylamine; In chloroform; tert-butyl alcohol;

upstream raw materials:

N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N²-<2-(triphenylphosphonio)ethoxycarbonyl>asparagin-benzylester-chlorid

{2-[(S)-1-Benzyloxycarbonyl-2-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylcarbamoyl)-ethylcarbamoyloxy]-ethyl}-triphenyl-phosphonium

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

N-Peoc-Asparaginsaeure-benzylester

Downstream raw materials:

N-<2-(Triphenylphophonio)ethoxycarbonyl>leucyl-N⁴-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)asparagin-benzylester-chlorid

N-<2-(Triphenylphophonio)ethoxycarbonyl>phenylalanyl-N⁴-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)asparagin-benzylester-chlorid

Seryl-N⁴-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)asparagin-benzylester-chlorid

N-<2-(Triphenylphophonio)ethoxycarbonyl>methionyl-seryl-N⁴-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)asparagin-benzylester-chlorid

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