p-nitrophenyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-β-D-glucopyranoside

Base Information

• Chemical Name: p-nitrophenyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-β-D-glucopyranoside
• CAS No.: 84594-49-0
• Molecular Formula: C₂₉H₃₀N₂O₉
• Molecular Weight: 550.565
• Mol file: 84594-49-0.mol

Synonyms:p-nitrophenyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-β-D-glucopyranoside

Chemical Property of p-nitrophenyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrophenyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-β-D-glucopyranoside

There total 1 articles about p-nitrophenyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-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:

benzyl bromide (100-39-0) + N-[(2R,4aR,6S,7R,8R,8aS)-8-Hydroxy-2-(4-methoxy-phenyl)-6-(4-nitro-phenoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (171233-52-6) → p-nitrophenyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-β-D-glucopyranoside (84594-49-0)

Guidance literature:

With barium dihydroxide; barium carbonate; In N,N-dimethyl-formamide; for 1.5h; Yield given; Ambient temperature;

DOI:10.1016/0008-6215(82)85025-8

Reference yield: 68.0%

p-nitrophenyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-β-D-glucopyranoside (84594-49-0) → p-nitrophenyl 2-acetamido-3-O-benzyl-2-deoxy-β-D-glucopyranoside (84564-21-6)

Guidance literature:

With acetic acid; In water; for 0.166667h;

DOI:10.1016/0008-6215(82)85025-8

Reference yield:

p-nitrophenyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-β-D-glucopyranoside (84594-49-0) → p-trifluoroacetamidophenyl 2-acetamido-2-deoxy-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranoside (84564-26-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 68 percent / AcOH / H₂O / 0.17 h

2: 41 percent / BaCO₃, Ba(OH)2 * 8 H₂O / dimethylformamide / 2 h

3: 57 percent / silver trifluoromethanesulfonate, 2,4,6-trimethylpyridine / toluene; nitromethane / Ambient temperature

4: H₂ / Adams's catalyst / ethyl acetate

5: pyridine / ethyl acetate / 0.5 h / 60 °C

6: 66 percent / H₂ / 10percent Pd-C / acetic acid

With pyridine; 2,4,6-trimethyl-pyridine; barium dihydroxide; hydrogen; silver trifluoromethanesulfonate; acetic acid; barium carbonate; platinum(IV) oxide; palladium on activated charcoal; In nitromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0008-6215(82)85025-8

upstream raw materials:

benzyl bromide

N-[(2R,4aR,6S,7R,8R,8aS)-8-Hydroxy-2-(4-methoxy-phenyl)-6-(4-nitro-phenoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Downstream raw materials:

p-nitrophenyl 2-acetamido-3-O-benzyl-2-deoxy-β-D-glucopyranoside

p-nitrophenyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

p-nitrophenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

p-trifluoroacetamidophenyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-β-D-glucopyranoside