p-nitrophenyl O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1-3)-4-O-benzoyl-2-O-benzyl-β-D-mannopyranoside

Base Information

• Chemical Name: p-nitrophenyl O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1-3)-4-O-benzoyl-2-O-benzyl-β-D-mannopyranoside
• CAS No.: 102717-24-8
• Molecular Formula: C₆₀H₅₁NO₁₈
• Molecular Weight: 1074.06
• Mol file: 102717-24-8.mol

Synonyms:p-nitrophenyl O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1-3)-4-O-benzoyl-2-O-benzyl-β-D-mannopyranoside

Chemical Property of p-nitrophenyl O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1-3)-4-O-benzoyl-2-O-benzyl-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrophenyl O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1-3)-4-O-benzoyl-2-O-benzyl-β-D-mannopyranoside

There total 9 articles about p-nitrophenyl O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1-3)-4-O-benzoyl-2-O-benzyl-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: 90.0%

C79H65NO18 (102717-23-7) → p-nitrophenyl O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1-3)-4-O-benzoyl-2-O-benzyl-β-D-mannopyranoside (102717-24-8)

Guidance literature:

With acetic acid;

DOI:10.1016/0008-6215(85)85024-2

Reference yield:

4-nitrophenyl-β-D-mannopyranoside (35599-02-1) → p-nitrophenyl O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1-3)-4-O-benzoyl-2-O-benzyl-β-D-mannopyranoside (102717-24-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 52 percent / p-toluenesulfonic acid / dimethylformamide / 2 h / Ambient temperature

2: 59 percent / pyridine / -38 - 20 °C

3: 73 percent / triflic acid / cyclohexane; CH₂Cl₂ / Ambient temperature

4: 69 percent / NaOMe / methanol / 0.5 h / Heating

5: 89 percent / silver triflate, 2,4,6-collidine / toluene; nitromethane / 0.25 h / -25 °C

6: 88 percent / 90percent aq. AcOH / 1 h / 100 °C

7: pyridine / 48 h / Ambient temperature

8: pyridine

9: 90 percent / 90percent aq. AcOH

With pyridine; 2,4,6-trimethyl-pyridine; trifluorormethanesulfonic acid; sodium methylate; silver trifluoromethanesulfonate; acetic acid; toluene-4-sulfonic acid; In methanol; nitromethane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0008-6215(85)85024-2

Reference yield:

2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide (14218-11-2,14218-30-5,61198-88-7,108438-33-1,108836-02-8,114682-36-9,127305-34-4,151377-77-4) → p-nitrophenyl O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1-3)-4-O-benzoyl-2-O-benzyl-β-D-mannopyranoside (102717-24-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / silver triflate, 2,4,6-collidine / toluene; nitromethane / 0.25 h / -25 °C

2: 88 percent / 90percent aq. AcOH / 1 h / 100 °C

3: pyridine / 48 h / Ambient temperature

4: pyridine

5: 90 percent / 90percent aq. AcOH

With pyridine; 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate; acetic acid; In nitromethane; toluene;

DOI:10.1016/0008-6215(85)85024-2

upstream raw materials:

C₇₉H₆₅NO₁₈

2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide

4-nitrophenyl-β-D-mannopyranoside

p-nitrophenyl 4,6-O-cyclohexylidene-β-D-mannopyranoside

Downstream raw materials:

p-nitrophenyl O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1-3)-O<2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl>-(1-6)-4-O-benzyl-2-O-benzyl-β-D-mannopyranoside