6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl bromide

Base Information

• Chemical Name: 6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl bromide
• CAS No.: 334834-28-5
• Molecular Formula: C₂₉H₂₈BrNO₁₀
• Molecular Weight: 630.446
• Mol file: 334834-28-5.mol

Synonyms:6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl bromide

Chemical Property of 6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl bromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl bromide

There total 4 articles about 6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl bromide 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: 94.0%

acetic anhydride (108-24-7) + 6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl acetate (334834-27-4) → 6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl bromide (334834-28-5)

Guidance literature:

With acetic acid; for 8h;

DOI:10.1021/ja003508a

Reference yield:

1,6-anhydro-2,4-di-O-benzyl-β-D-mannopyranose (86861-42-9) → 6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl bromide (334834-28-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / DMAP; Et₃N / tetrahydrofuran / 12 h / 20 °C

2: 88 percent / TFA / 10 h / 20 °C

3: 94 percent / 30percent HBr; AcOH / 8 h

With dmap; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/ja003508a

Reference yield:

4-Nitrophenyl chloroformate (7693-46-1) → 6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl bromide (334834-28-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / DMAP; Et₃N / tetrahydrofuran / 12 h / 20 °C

2: 88 percent / TFA / 10 h / 20 °C

3: 94 percent / 30percent HBr; AcOH / 8 h

With dmap; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/ja003508a

upstream raw materials:

acetic anhydride

6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl acetate

1,6-anhydro-2,4-di-O-benzyl-β-D-mannopyranose

4-Nitrophenyl chloroformate

Downstream raw materials:

2-O-{6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl}-4-O-benzoyl-3-O-benzyl-1,6-anhydro-β-L-gulopyranose