p-nitrophenyl 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-3-O-benzyl-2-deoxy-β-D-mannopyranoside

Base Information

• Chemical Name: p-nitrophenyl 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-3-O-benzyl-2-deoxy-β-D-mannopyranoside
• CAS No.: 140686-55-1
• Molecular Formula: C₃₃H₃₉N₅O₁₅
• Molecular Weight: 745.697
• Mol file: 140686-55-1.mol

Synonyms:p-nitrophenyl 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-3-O-benzyl-2-deoxy-β-D-mannopyranoside

Chemical Property of p-nitrophenyl 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-3-O-benzyl-2-deoxy-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrophenyl 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-3-O-benzyl-2-deoxy-β-D-mannopyranoside

There total 7 articles about p-nitrophenyl 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-3-O-benzyl-2-deoxy-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: 99.0%

p-nitrophenyl 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside (140686-54-0) → p-nitrophenyl 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-3-O-benzyl-2-deoxy-β-D-mannopyranoside (140686-55-1)

Guidance literature:

With triethylamine hydrofluoride; In tetrahydrofuran;

DOI:10.1016/0008-6215(92)80050-B

Reference yield:

ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (99409-32-2) → p-nitrophenyl 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-3-O-benzyl-2-deoxy-β-D-mannopyranoside (140686-55-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / dimethyl(methylthio)sulfonium triflate, 2,6-di-tert-butyl-4-methylpyridine, molecular sieves / CH₂Cl₂ / 3 h / Ambient temperature

2: 1) hydrazine hydrate, 2) pyridine / 1) ethanol, reflux, overnight

3: 99 percent / triethylammonium fluoride / tetrahydrofuran

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; molecular sieve; hydrazine hydrate; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine hydrofluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0008-6215(92)80050-B

Reference yield:

benzyl bromide (100-39-0) → p-nitrophenyl 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-3-O-benzyl-2-deoxy-β-D-mannopyranoside (140686-55-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / sodium hydride / dimethylformamide / 1 h / Ambient temperature

2: 1) aq. 70percent acetic acid, 2) pyridine / 1) 70 deg C, 1.5 h, 2) overnight

3: 96 percent / dimethyl(methylthio)sulfonium triflate, 2,6-di-tert-butyl-4-methylpyridine, molecular sieves / CH₂Cl₂ / 3 h / Ambient temperature

4: 1) hydrazine hydrate, 2) pyridine / 1) ethanol, reflux, overnight

5: 99 percent / triethylammonium fluoride / tetrahydrofuran

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; molecular sieve; sodium hydride; hydrazine hydrate; acetic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine hydrofluoride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)80050-B

upstream raw materials:

p-nitrophenyl 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside

ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

benzyl bromide

p-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside

Downstream raw materials:

p-trifluoroacetamidophenyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-mannopyranosiduronic acid

tert-butyl uronate

tert-butyl uronate

tert-butyl uronate

Refernces