4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3-O-acetyl-4,6-di-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside

Base Information

• Chemical Name: 4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3-O-acetyl-4,6-di-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside
• CAS No.: 150161-32-3
• Molecular Formula: C₄₀H₅₄N₂O₂₄
• Molecular Weight: 946.868
• Mol file: 150161-32-3.mol

Synonyms:4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3-O-acetyl-4,6-di-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside

Chemical Property of 4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3-O-acetyl-4,6-di-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3-O-acetyl-4,6-di-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside

There total 10 articles about 4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3-O-acetyl-4,6-di-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-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: 78.0%

4-nitrophenyl 2,3-di-O-acetyl-β-D-glucopyranoside (40837-80-7) + O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-3-O-acetyl-4,6-di-O-methyl-α-D-mannopyranosyl bromide (150161-31-2) → 4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3-O-acetyl-4,6-di-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside (150161-32-3)

Guidance literature:

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 6h;

DOI:10.1016/0008-6215(93)84079-L

Reference yield:

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((2S,3S,4S,5R,6R)-4-benzyloxy-2,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester (150161-26-5) → 4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3-O-acetyl-4,6-di-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside (150161-32-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / H₂ / 10percent Pd/C / acetic acid / 48 h / 2587.7 Torr / Ambient temperature

2: 98 percent / pyridine / Ambient temperature

3: 81 percent / conc. H₂SO₄ / 17 h / Ambient temperature

4: 90 percent / 31percentHBr/AcOH / CH₂Cl₂ / 12 h / 0 °C

5: 78 percent / s-collidine, CF₃SO₃Ag, 4A molecular sieves / CH₂Cl₂ / 6 h / 0 °C

With pyridine; 2,4,6-trimethyl-pyridine; 4 A molecular sieve; sulfuric acid; hydrogen bromide; hydrogen; silver trifluoromethanesulfonate; acetic acid; palladium on activated charcoal; In dichloromethane; acetic acid;

DOI:10.1016/0008-6215(93)84079-L

Reference yield:

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-amino-6-((2S,3S,4S,5R,6R)-4-benzyloxy-2,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester → 4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3-O-acetyl-4,6-di-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside (150161-32-3)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / Ambient temperature

2: 89 percent / H₂ / 10percent Pd/C / acetic acid / 48 h / 2587.7 Torr / Ambient temperature

3: 98 percent / pyridine / Ambient temperature

4: 81 percent / conc. H₂SO₄ / 17 h / Ambient temperature

5: 90 percent / 31percentHBr/AcOH / CH₂Cl₂ / 12 h / 0 °C

6: 78 percent / s-collidine, CF₃SO₃Ag, 4A molecular sieves / CH₂Cl₂ / 6 h / 0 °C

With pyridine; 2,4,6-trimethyl-pyridine; 4 A molecular sieve; sulfuric acid; hydrogen bromide; hydrogen; silver trifluoromethanesulfonate; acetic acid; palladium on activated charcoal; In dichloromethane; acetic acid;

DOI:10.1016/0008-6215(93)84079-L

upstream raw materials:

4-nitrophenyl 2,3-di-O-acetyl-β-D-glucopyranoside

O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-3-O-acetyl-4,6-di-O-methyl-α-D-mannopyranosyl bromide

Methyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-4,6-di-O-methyl-α-D-mannopyranoside

Methyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-3-O-acetyl-4,6-di-O-methyl-α-D-mannopyranoside

Downstream raw materials:

4-Nitrophenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(4,6-di-O-methyl-α-D-mannopyranosyl)-(1->6)-β-D-glucopyranoside