Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acetylamino-phenoxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acetylamino-phenoxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 170940-41-7
• Molecular Formula: C₂₂H₂₇NO₁₁
• Molecular Weight: 481.456
• Mol file: 170940-41-7.mol

Synonyms:Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acetylamino-phenoxy)-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acetylamino-phenoxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acetylamino-phenoxy)-tetrahydro-pyran-3-yl ester

There total 4 articles about Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acetylamino-phenoxy)-tetrahydro-pyran-3-yl ester 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: 100.0%

4-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-66-4,5987-78-0,13242-51-8,14131-42-1,17042-39-6,30902-95-5,40269-27-0,58918-67-5,67672-66-6,67968-31-4,72002-91-6,76549-82-1,89195-78-8,89195-79-9) + acetic anhydride (108-24-7) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acetylamino-phenoxy)-tetrahydro-pyran-3-yl ester (170940-41-7)

Guidance literature:

4-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside; With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate; at 20 ℃; for 5.5h;

acetic anhydride; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 35h; Inert atmosphere;

DOI:10.1039/c8cc06068a

Reference yield:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acetylamino-phenoxy)-tetrahydro-pyran-3-yl ester (170940-41-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrabutylammomium bromide; sodium hydroxide / chloroform; water

2.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 5.5 h / 20 °C

2.2: 35 h / 20 °C / Inert atmosphere

With palladium 10% on activated carbon; tetrabutylammomium bromide; hydrogen; sodium hydroxide; In methanol; chloroform; water; ethyl acetate;

DOI:10.1039/c8cc06068a

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acetylamino-phenoxy)-tetrahydro-pyran-3-yl ester (170940-41-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrabutylammomium bromide; sodium hydroxide / chloroform; water

2.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 5.5 h / 20 °C

2.2: 35 h / 20 °C / Inert atmosphere

With palladium 10% on activated carbon; tetrabutylammomium bromide; hydrogen; sodium hydroxide; In methanol; chloroform; water; ethyl acetate;

DOI:10.1039/c8cc06068a

upstream raw materials:

acetic anhydride

p-aminophenyl β-D-galactopyranoside

4-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

Downstream raw materials:

p-acetamidophenyl β-D-galactopyranoside

β-D-galactose peracetate