1-bromo-2,3,4-tri-O-acetyl-α-D-galactopyranuronic acid methyl ester

Base Information

• Chemical Name: 1-bromo-2,3,4-tri-O-acetyl-α-D-galactopyranuronic acid methyl ester
• CAS No.: 56768-32-2
• Molecular Formula: C₁₃H₁₇BrO₉
• Molecular Weight: 397.177
• Mol file: 56768-32-2.mol

Synonyms:1-bromo-2,3,4-tri-O-acetyl-α-D-galactopyranuronic acid methyl ester

Chemical Property of 1-bromo-2,3,4-tri-O-acetyl-α-D-galactopyranuronic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-bromo-2,3,4-tri-O-acetyl-α-D-galactopyranuronic acid methyl ester

There total 2 articles about 1-bromo-2,3,4-tri-O-acetyl-α-D-galactopyranuronic acid methyl 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: 81.0%

methyl (1,2,3,4-tetra-O-acetyl-α,β-D-galactopyranosid) uronate (40269-24-7) → (2S,3R,4S,5R)-3,4,5-Triacetoxy-6-bromo-tetrahydro-pyran-2-carboxylic acid methyl ester (6919-98-8,21085-72-3,56768-32-2,57820-69-6,108032-44-6)

Guidance literature:

With hydrogen bromide; In acetic acid;

DOI:10.1016/0008-6215(82)84017-2

Reference yield:

methyl D-galactopyranuronate (18486-47-0,18490-93-2,28817-88-1,82228-14-6) → (2S,3R,4S,5R)-3,4,5-Triacetoxy-6-bromo-tetrahydro-pyran-2-carboxylic acid methyl ester (6919-98-8,21085-72-3,56768-32-2,57820-69-6,108032-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: 81 percent / 30percent HBr / acetic acid

With hydrogen bromide; In pyridine; acetic acid;

DOI:10.1016/0008-6215(82)84017-2

Reference yield: 89.5%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 1-bromo-2,3,4-tri-O-acetyl-α-D-galactopyranuronic acid methyl ester (56768-32-2) → p-nitrophenyl-2,3,4-tri-O-acetyl-beta-D-galacturonic acid methyl ester

Guidance literature:

4-nitro-phenol; With iodine; silver carbonate; In dichloromethane; for 0.166667h; Molecular sieve; Inert atmosphere;

1-bromo-2,3,4-tri-O-acetyl-α-D-galactopyranuronic acid methyl ester; In dichloromethane; for 24h;

upstream raw materials:

methyl (1,2,3,4-tetra-O-acetyl-α,β-D-galactopyranosid) uronate

methyl D-galactopyranuronate

Downstream raw materials:

benzyl-2,3,6,2',6'-penta-O-benzyl-3'-O--β-D-lactoside

methyl (2,3,4-tri-O-acetyl-β-D-galactopyranosyl azide)uronate

methyl (benzyl 2,3,4-tri-O-acetyl-β-D-galactopyranosid)uronate

3,4,5-trihydroxy-6-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester