4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: 4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 848568-08-1
• Molecular Formula: C₃₂H₄₃NO₁₄
• Molecular Weight: 665.692

Synonyms:4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside

Chemical Property of 4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

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Technology Process of 4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside

There total 11 articles about 4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside 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: 85.0%

4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-2-deoxy-β-D-glucopyranoside (848568-07-0) + benzoyl cyanide (613-90-1) → 4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside (848568-08-1)

Guidance literature:

With triethylamine; In acetonitrile; at -40 ℃; for 0.5h;

DOI:10.1016/j.tetasy.2004.11.066

Reference yield:

tris(trimethylsilyl)fucosyl iodide → 4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside (848568-08-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 2,6-di-tert-butylpyridine / CH₂Cl₂ / 5 h / 20 °C

2: methanol / CH₂Cl₂ / 1 h

3: 2.2 g / pyridine / 20 °C

4: 98 percent / trifluoroacetic acid; water / CH₂Cl₂ / 1 h / 20 °C

5: 85 percent / triethylamine / acetonitrile / 0.5 h / -40 °C

With pyridine; methanol; 2,6-di-tert-butyl-pyridine; water; triethylamine; trifluoroacetic acid; In dichloromethane; acetonitrile;

DOI:10.1016/j.tetasy.2004.11.066

Reference yield:

4-pentenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside → 4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside (848568-08-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 2,6-di-tert-butylpyridine / CH₂Cl₂ / 5 h / 20 °C

2: methanol / CH₂Cl₂ / 1 h

3: 2.2 g / pyridine / 20 °C

4: 98 percent / trifluoroacetic acid; water / CH₂Cl₂ / 1 h / 20 °C

5: 85 percent / triethylamine / acetonitrile / 0.5 h / -40 °C

With pyridine; methanol; 2,6-di-tert-butyl-pyridine; water; triethylamine; trifluoroacetic acid; In dichloromethane; acetonitrile;

DOI:10.1016/j.tetasy.2004.11.066

upstream raw materials:

4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-2-deoxy-β-D-glucopyranoside

benzoyl cyanide

2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate

n-Pent-4-enyl alcohol

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