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

Base Information

• Chemical Name: 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
• CAS No.: 583041-06-9
• Molecular Formula: C₅₈H₅₆N₄O₁₉
• Molecular Weight: 1113.1
• Mol file: 583041-06-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 16 articles about 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 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: 62.2%

(2S,3R,4S,5S,6R)-5-azido-2-methyl-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4-diyl diacetate (583041-03-6) + 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) → 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 (583041-06-9)

Guidance literature:

With 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at -30 ℃; for 0.5h;

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 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 (583041-06-9)

Guidance literature:

Multi-step reaction with 7 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

7: 62.2 percent / triethylsilyl trifluoromethanesulfonate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / -30 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; 4 A molecular sieve; boron trifluoride diethyl etherate; triethylsilyl trifluoromethyl sulfonate; 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 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 (583041-06-9)

Guidance literature:

Multi-step reaction with 7 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

7.1: 62.2 percent / triethylsilyl trifluoromethanesulfonate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / -30 °C

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; 10-camphorsufonic acid; triethylsilyl trifluoromethyl sulfonate; 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:

(2S,3R,4S,5S,6R)-5-azido-2-methyl-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4-diyl diacetate

4-methoxyphenyl 4,6-O-benzylidene-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

Downstream raw materials:

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-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