5-benzyloxycarbonylamino-1-pentyl α-L-fucopyranosyl-(1→?2)-β-D-galactopyranosyl-(1?→4)-2-acetamide-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: 5-benzyloxycarbonylamino-1-pentyl α-L-fucopyranosyl-(1→?2)-β-D-galactopyranosyl-(1?→4)-2-acetamide-2-deoxy-β-D-glucopyranoside
• CAS No.: 1603850-89-0
• Molecular Formula: C₃₃H₅₂N₂O₁₇
• Molecular Weight: 748.779

Synonyms:5-benzyloxycarbonylamino-1-pentyl α-L-fucopyranosyl-(1→?2)-β-D-galactopyranosyl-(1?→4)-2-acetamide-2-deoxy-β-D-glucopyranoside

Chemical Property of 5-benzyloxycarbonylamino-1-pentyl α-L-fucopyranosyl-(1→?2)-β-D-galactopyranosyl-(1?→4)-2-acetamide-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of 5-benzyloxycarbonylamino-1-pentyl α-L-fucopyranosyl-(1→?2)-β-D-galactopyranosyl-(1?→4)-2-acetamide-2-deoxy-β-D-glucopyranoside

There total 12 articles about 5-benzyloxycarbonylamino-1-pentyl α-L-fucopyranosyl-(1→?2)-β-D-galactopyranosyl-(1?→4)-2-acetamide-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: 94.0%

5-benzyloxycarbonylamino-1-pentyl (2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1→?2)-(4,6-di-O-acetyl-β-D-galactopyranosyl)-(1?→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-β-D-glucopyranoside (1603850-62-9) + acetic anhydride (108-24-7) → 5-benzyloxycarbonylamino-1-pentyl α-L-fucopyranosyl-(1→?2)-β-D-galactopyranosyl-(1?→4)-2-acetamide-2-deoxy-β-D-glucopyranoside (1603850-89-0)

Guidance literature:

5-benzyloxycarbonylamino-1-pentyl (2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1→?2)-(4,6-di-O-acetyl-β-D-galactopyranosyl)-(1?→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-β-D-glucopyranoside; With sodium methylate; In methanol; at 0 - 20 ℃; for 4h; Inert atmosphere;

With hydrazine hydrate; In ethanol; for 6.5h; Reflux; Inert atmosphere;

acetic anhydride; In methanol; dichloromethane; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.3390/molecules19010414

Reference yield:

C36H47NO17S → 5-benzyloxycarbonylamino-1-pentyl α-L-fucopyranosyl-(1→?2)-β-D-galactopyranosyl-(1?→4)-2-acetamide-2-deoxy-β-D-glucopyranoside (1603850-89-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: trifluoroacetic acid / water / 2 h / 0 - 20 °C / Inert atmosphere

2.1: dibutyltin chloride / acetone / 0.17 h / 20 °C / Inert atmosphere

2.2: 0.33 h / 20 °C / Inert atmosphere

3.1: cyclopentyl methyl ether / dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

3.2: 5.5 h / -80 °C / Molecular sieve; Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 0.67 h / 0 - 20 °C / Inert atmosphere

5.1: pyridine / 2 h / 0 - 20 °C / Inert atmosphere

6.1: N-iodo-succinimide / 1 h / Inert atmosphere

6.2: 0.67 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

6.3: 30 h / 0 °C / Inert atmosphere

7.1: zinc; acetic acid / dichloromethane / 1 h / 40 °C

8.1: sodium methylate / methanol / 4 h / 0 - 20 °C / Inert atmosphere

8.2: 6.5 h / Reflux; Inert atmosphere

8.3: 1.5 h / 20 °C / Inert atmosphere

With pyridine; N-iodo-succinimide; cyclopentyl methyl ether; dibutyltin chloride; sodium methylate; acetic acid; trifluoroacetic acid; zinc; In methanol; dichloromethane; water; acetone;

DOI:10.3390/molecules19010414

Reference yield:

ethyl [4,6-di-O-acetyl-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-galactopyranosyl]-(1→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-1-thio-β-D-glucopyranoside (1603850-44-7) → 5-benzyloxycarbonylamino-1-pentyl α-L-fucopyranosyl-(1→?2)-β-D-galactopyranosyl-(1?→4)-2-acetamide-2-deoxy-β-D-glucopyranoside (1603850-89-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: cyclopentyl methyl ether / dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

1.2: 5.5 h / -80 °C / Molecular sieve; Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 0.67 h / 0 - 20 °C / Inert atmosphere

3.1: pyridine / 2 h / 0 - 20 °C / Inert atmosphere

4.1: N-iodo-succinimide / 1 h / Inert atmosphere

4.2: 0.67 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

4.3: 30 h / 0 °C / Inert atmosphere

5.1: zinc; acetic acid / dichloromethane / 1 h / 40 °C

6.1: sodium methylate / methanol / 4 h / 0 - 20 °C / Inert atmosphere

6.2: 6.5 h / Reflux; Inert atmosphere

6.3: 1.5 h / 20 °C / Inert atmosphere

With pyridine; N-iodo-succinimide; cyclopentyl methyl ether; sodium methylate; acetic acid; trifluoroacetic acid; zinc; In methanol; dichloromethane;

DOI:10.3390/molecules19010414

upstream raw materials:

5-benzyloxycarbonylamino-1-pentyl (2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1→?2)-(4,6-di-O-acetyl-β-D-galactopyranosyl)-(1?→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-β-D-glucopyranoside

acetic anhydride

ethyl (4,6-di-O-acetyl-β-D-galactopyranosyl)-(1→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-1-thio-β-D-glucopyranoside

2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-1,3,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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