4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: 4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
• CAS No.: 583041-05-8
• Molecular Formula: C₄₈H₄₃NO₁₄
• Molecular Weight: 857.868

Synonyms:4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

Chemical Property of 4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

There total 12 articles about 4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 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: 91.0%

4-methoxyphenyl 4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside (583041-04-7) → 4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside (583041-05-8)

Guidance literature:

With sodium hydrogencarbonate; thiourea; In methanol; dichloromethane; at 25 ℃; for 1h;

DOI:10.1081/CAR-120020480

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → 4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside (583041-05-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 62.5 percent / BF₃*Et₂O / CH₂Cl₂ / 22 h

2: 69.5 percent / sodium methoxide / methanol / 3 h

3: 77.5 percent / p-toluenesulfonic acid; molecular sieves 3 Angstroem / acetonitrile

4: 83 percent / triethylamine / CH₂Cl₂ / 3 h

5: 54.9 percent / N-iodosuccinimide; trifluoromethanesulfonic acid; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.75 h

6: 91 percent / thiourea; NaHCO₃ / methanol; CH₂Cl₂ / 1 h / 25 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; thiourea; In methanol; dichloromethane; acetonitrile;

DOI:10.1081/CAR-120020480

Reference yield:

4-methoxyphenyl α-L-rhamnopyranoside (18918-36-0) → 4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside (583041-05-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 73 percent / p-toluenesulfonic acid / dimethylformamide / 5 h / 20 °C

2.1: 92 percent / pyridine / 4 h / 20 °C

3.1: 83.5 percent / acetic acid / H₂O / 2 h / 80 °C

4.1: (+/-) camphor-10-sulfonic acid / CH₂Cl₂ / 0.25 h

4.2: 2.68 g / acetic acid / H₂O / 0.5 h / 20 °C

5.1: 54.9 percent / N-iodosuccinimide; trifluoromethanesulfonic acid; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.75 h

6.1: 91 percent / thiourea; NaHCO₃ / methanol; CH₂Cl₂ / 1 h / 25 °C

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; 10-camphorsufonic acid; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; thiourea; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1081/CAR-120020480

upstream raw materials:

4-methoxyphenyl 4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

4-methoxyphenyl α-L-rhamnopyranoside

4-methoxyphenyl 2,3,4-tetra-O-acetyl-α-L-rhamnopyranoside

Downstream raw materials:

4-methoxyphenyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-α-L-fucopyranosyl-(1->3)-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

4-methoxyphenyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-α-L-fucopyranosyl-(1->3)-4,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranoside

4-methoxyphenyl 2-azido-3,4-di-O-acetyl-2-deoxy-α-L-fucopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

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