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

Base Information

• Chemical Name: 6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl acetate
• CAS No.: 334834-27-4
• Molecular Formula: C₃₁H₃₁NO₁₂
• Molecular Weight: 609.587
• Mol file: 334834-27-4.mol

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

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

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 acetate

There total 3 articles about 6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl acetate 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: 88.0%

acetic anhydride (108-24-7) + 2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-1,6-anhydro-β-D-mannopyranose (334834-26-3) → 6-O-acetyl-2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-α-D-mannopyranosyl acetate (334834-27-4)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 10h;

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 acetate (334834-27-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 88 percent / TFA / 10 h / 20 °C

With dmap; 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 acetate (334834-27-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 88 percent / TFA / 10 h / 20 °C

With dmap; triethylamine; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/ja003508a

upstream raw materials:

acetic anhydride

2,4-di-O-benzyl-3-O-[(p-nitrophenyl)formyl]-1,6-anhydro-β-D-mannopyranose

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

4-Nitrophenyl chloroformate

Downstream raw materials:

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

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