4-nitrophenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)-2,3-O-isopropylidene-β-D-mannopyranoside

Base Information

• Chemical Name: 4-nitrophenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)-2,3-O-isopropylidene-β-D-mannopyranoside
• CAS No.: 126777-67-1
• Molecular Formula: C₂₉H₄₂N₂O₁₈
• Molecular Weight: 706.655
• Mol file: 126777-67-1.mol

Synonyms:4-nitrophenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)-2,3-O-isopropylidene-β-D-mannopyranoside

Chemical Property of 4-nitrophenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)-2,3-O-isopropylidene-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-nitrophenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)-2,3-O-isopropylidene-β-D-mannopyranoside

There total 12 articles about 4-nitrophenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)-2,3-O-isopropylidene-β-D-mannopyranoside 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: 67.0%

4-nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)(1->6)-2,3-O-isopropylidene-β-D-mannopyranoside (126777-66-0) → 4-nitrophenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)-2,3-O-isopropylidene-β-D-mannopyranoside (126777-67-1)

Guidance literature:

With sodium methylate; In methanol; Ambient temperature;

DOI:10.1016/0008-6215(89)85112-2

Reference yield:

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside (20672-67-7) → 4-nitrophenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)-2,3-O-isopropylidene-β-D-mannopyranoside (126777-67-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) silver trifluoromethanesulfonate, 2,4,6-trimethylpyridine, 2.) 4A molecular sieves, hydrazine hydrate, 3.) pyridine / 1.) CH₂Cl₂, 4.5 h, 2.) ethanol, 3 h, 3.) 90 deg C, 30 min

2: H₂ / 10percent Pd-C / acetic acid / 24 h / 2587.7 Torr / Ambient temperature

3: 72.5 percent / pyridine / Ambient temperature

4: 90 percent / 1percent conc. H₂SO₄ / 12 h / Ambient temperature

5: 79 percent / 31percent HBr / CH₂Cl₂; acetic acid / 12 h / 0 °C

6: 66.5 percent / Hg(CN)2, molecular sieves 4 Angstroem / acetonitrile / 3 h / Ambient temperature

7: 67 percent / sodium methoxide / methanol / Ambient temperature

With pyridine; 2,4,6-trimethyl-pyridine; 4 A molecular sieve; sulfuric acid; hydrogen bromide; hydrogen; sodium methylate; silver trifluoromethanesulfonate; mercury(II) cyanide; hydrazine hydrate; palladium on activated charcoal; In methanol; dichloromethane; acetic acid; acetonitrile;

DOI:10.1016/0008-6215(89)85112-2

Reference yield:

methyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside (126777-56-8) → 4-nitrophenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)-2,3-O-isopropylidene-β-D-mannopyranoside (126777-67-1)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂ / 10percent Pd-C / acetic acid / 24 h / 2587.7 Torr / Ambient temperature

2: 72.5 percent / pyridine / Ambient temperature

3: 90 percent / 1percent conc. H₂SO₄ / 12 h / Ambient temperature

4: 79 percent / 31percent HBr / CH₂Cl₂; acetic acid / 12 h / 0 °C

5: 66.5 percent / Hg(CN)2, molecular sieves 4 Angstroem / acetonitrile / 3 h / Ambient temperature

6: 67 percent / sodium methoxide / methanol / Ambient temperature

With pyridine; 4 A molecular sieve; sulfuric acid; hydrogen bromide; hydrogen; sodium methylate; mercury(II) cyanide; palladium on activated charcoal; In methanol; dichloromethane; acetic acid; acetonitrile;

DOI:10.1016/0008-6215(89)85112-2

upstream raw materials:

4-nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)(1->6)-2,3-O-isopropylidene-β-D-mannopyranoside

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside

4-nitrophenyl-β-D-mannopyranoside

2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl bromide

Downstream raw materials:

4-nitrophenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl)(1->6)-β-D-mannopyranoside