p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→4)-2-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-β-L-fucopyranoside

Base Information

• Chemical Name: p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→4)-2-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-β-L-fucopyranoside
• CAS No.: 1419180-56-5
• Molecular Formula: C₅₉H₆₁N₃O₂₀
• Molecular Weight: 1132.14

Synonyms:p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→4)-2-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-β-L-fucopyranoside

Chemical Property of p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→4)-2-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-β-L-fucopyranoside

Chemical Property:

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Technology Process of p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→4)-2-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-β-L-fucopyranoside

There total 7 articles about p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→4)-2-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-β-L-fucopyranoside 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: 80.0%

p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→4)-2-O-benzyl-β-L-fucopyranoside (1419180-55-4) + 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyltrichloroacetimidate (83025-20-1) → p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→4)-2-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-β-L-fucopyranoside (1419180-56-5)

Guidance literature:

With silica-gel-supported sulfuric acid; In dichloromethane; at -40 ℃; for 2h; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1039/c2ra22407k

Reference yield:

C13H18O6 (1419180-51-0) → p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→4)-2-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-β-L-fucopyranoside (1419180-56-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: camphor-10-sulfonic acid / acetone / 2 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 20 °C

3.1: acetic acid; water / 2 h / 80 °C

4.1: di(n-butyl)tin oxide / methanol / 2 h / Reflux

4.2: 12 h / 60 °C

5.1: silica-gel-supported sulfuric acid; N-iodo-succinimide / dichloromethane / 1.5 h / 5 - 10 °C / Inert atmosphere; Molecular sieve

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 20 °C

7.1: silica-gel-supported sulfuric acid / dichloromethane / 2 h / -40 °C / Inert atmosphere; Molecular sieve

With N-iodo-succinimide; silica-gel-supported sulfuric acid; camphor-10-sulfonic acid; water; sodium hydride; di(n-butyl)tin oxide; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; mineral oil;

DOI:10.1039/c2ra22407k

Reference yield:

p-methoxyphenyl 3,4-O-isopropylidene-β-L-fucopyranoside (1419180-50-9) → p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→4)-2-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-β-L-fucopyranoside (1419180-56-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 20 °C

2.1: acetic acid; water / 2 h / 80 °C

3.1: di(n-butyl)tin oxide / methanol / 2 h / Reflux

3.2: 12 h / 60 °C

4.1: silica-gel-supported sulfuric acid; N-iodo-succinimide / dichloromethane / 1.5 h / 5 - 10 °C / Inert atmosphere; Molecular sieve

5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 20 °C

6.1: silica-gel-supported sulfuric acid / dichloromethane / 2 h / -40 °C / Inert atmosphere; Molecular sieve

With N-iodo-succinimide; silica-gel-supported sulfuric acid; water; sodium hydride; di(n-butyl)tin oxide; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1039/c2ra22407k

upstream raw materials:

C₁₃H₁₈O₆

p-methoxyphenyl 3,4-O-isopropylidene-β-L-fucopyranoside

p-methoxyphenyl 2-O-benzyl-3,4-O-isopropylidene-β-L-fucopyranoside

C₂₀H₂₄O₆

Downstream raw materials:

p-methoxyphenyl β-D-glucopyranosyl-(1→4)-3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-β-L-fucopyranoside

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