p-nitrophenyl 4-O-benzyl-6-deoxy-2-O-methyl-α-D-mannopyranoside

Base Information

• Chemical Name: p-nitrophenyl 4-O-benzyl-6-deoxy-2-O-methyl-α-D-mannopyranoside
• CAS No.: 213386-03-9
• Molecular Formula: C₂₀H₂₃NO₇
• Molecular Weight: 389.405
• Mol file: 213386-03-9.mol

Synonyms:p-nitrophenyl 4-O-benzyl-6-deoxy-2-O-methyl-α-D-mannopyranoside

Chemical Property of p-nitrophenyl 4-O-benzyl-6-deoxy-2-O-methyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrophenyl 4-O-benzyl-6-deoxy-2-O-methyl-α-D-mannopyranoside

There total 7 articles about p-nitrophenyl 4-O-benzyl-6-deoxy-2-O-methyl-α-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: 90.0%

p-nitrophenyl 4-O-benzyl-6-deoxy-α-D-mannopyranoside (213386-02-8) + methyl iodide (74-88-4) → p-nitrophenyl 4-O-benzyl-6-deoxy-2-O-methyl-α-D-mannopyranoside (213386-03-9)

Guidance literature:

With tetrabutylammomium bromide; In sodium hydroxide; dichloromethane;

DOI:10.1016/S0008-6215(98)00074-3

Reference yield:

benzyl bromide (100-39-0) → p-nitrophenyl 4-O-benzyl-6-deoxy-2-O-methyl-α-D-mannopyranoside (213386-03-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / KOH / dimethylformamide / 0.67 h / 0 °C

2: 90 percent / CF₃CO₂H, H₂O / CH₂Cl₂ / 0.17 h / Ambient temperature

3: 90 percent / Bu₄NBr / CH₂Cl₂; aq. NaOH

With potassium hydroxide; tetrabutylammomium bromide; water; trifluoroacetic acid; In sodium hydroxide; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00074-3

Reference yield:

p-nitrophenyl 2,3-O-isopropylidene-α-D-mannopyranoside (80264-82-0) → p-nitrophenyl 4-O-benzyl-6-deoxy-2-O-methyl-α-D-mannopyranoside (213386-03-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / pyridine / 1.5 h / 60 °C

2: 73 percent / NaI / dimethylformamide / 5 h / 100 °C

3: 53 percent / LiAlH₄ / tetrahydrofuran / 20 h / Ambient temperature

4: 75 percent / KOH / dimethylformamide / 0.67 h / 0 °C

5: 90 percent / CF₃CO₂H, H₂O / CH₂Cl₂ / 0.17 h / Ambient temperature

6: 90 percent / Bu₄NBr / CH₂Cl₂; aq. NaOH

With potassium hydroxide; lithium aluminium tetrahydride; tetrabutylammomium bromide; water; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; pyridine; sodium hydroxide; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00074-3

upstream raw materials:

p-nitrophenyl 4-O-benzyl-6-deoxy-α-D-mannopyranoside

methyl iodide

benzyl bromide

p-nitrophenyl 2,3-O-isopropylidene-α-D-mannopyranoside

Downstream raw materials:

N-Benzyl-N-{(2S,3S,4R,5R,6S)-4-benzyloxy-6-[(2R,3R,4S,5S,6R)-3-benzyloxy-5-methoxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-5-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yl}-formamide