p-nitrophenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside

Base Information

• Chemical Name: p-nitrophenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside
• CAS No.: 140686-51-7
• Molecular Formula: C₂₆H₂₄N₄O₇
• Molecular Weight: 504.499
• Mol file: 140686-51-7.mol

Synonyms:p-nitrophenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside

Chemical Property of p-nitrophenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrophenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside

There total 1 articles about p-nitrophenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-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: 68.0%

benzyl bromide (100-39-0) + p-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside (140851-33-8) → p-nitrophenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside (140686-51-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 1h; Ambient temperature;

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

Reference yield:

p-nitrophenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside (140686-51-7) → p-trifluoroacetamidophenyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-mannopyranosiduronic acid (140686-60-8)

Guidance literature:

Multi-step reaction with 10 steps

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

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

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

4: 99 percent / triethylammonium fluoride / tetrahydrofuran

5: 32 percent / acetic anhydride, pyridinium dichromate / CH₂Cl₂ / Ambient temperature

6: 1) triphenylphosphine, 2) water / 1) CH₂Cl₂, r.t., overnight, 2) reflux, 12 h

7: pyridine / CH₂Cl₂ / 1 h / 0 °C

8: 1) aluminum amalgam, 2) pyridine / 1) aq. 80percent THF, r.t., 1 h, 2) CH₂Cl₂, 0 deg C, 1 h

9: 91 percent / hydrogen / 10percent Pd-C / ethyl acetate; H₂O / 3000.2 Torr

10: 1) formic acid, 2) sodium methoxide / 1) r.t., 6 h, 2) methanol, r.t., overnight

With pyridine; dipyridinium dichromate; formic acid; 2,6-di-tert-butyl-4-methylpyridine; molecular sieve; aluminium amalgam; water; hydrogen; sodium methylate; acetic anhydride; hydrazine hydrate; acetic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine hydrofluoride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

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

Reference yield:

p-nitrophenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside (140686-51-7) → tert-butyl uronate (140686-59-5)

Guidance literature:

Multi-step reaction with 9 steps

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

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

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

4: 99 percent / triethylammonium fluoride / tetrahydrofuran

5: 32 percent / acetic anhydride, pyridinium dichromate / CH₂Cl₂ / Ambient temperature

6: 1) triphenylphosphine, 2) water / 1) CH₂Cl₂, r.t., overnight, 2) reflux, 12 h

7: pyridine / CH₂Cl₂ / 1 h / 0 °C

8: 1) aluminum amalgam, 2) pyridine / 1) aq. 80percent THF, r.t., 1 h, 2) CH₂Cl₂, 0 deg C, 1 h

9: 91 percent / hydrogen / 10percent Pd-C / ethyl acetate; H₂O / 3000.2 Torr

With pyridine; dipyridinium dichromate; 2,6-di-tert-butyl-4-methylpyridine; molecular sieve; aluminium amalgam; water; hydrogen; acetic anhydride; hydrazine hydrate; acetic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine hydrofluoride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

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

upstream raw materials:

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

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

tert-butyl uronate

tert-butyl uronate