2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester

Base Information

• Chemical Name: 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester
• CAS No.: 6919-98-8
• Molecular Formula: C₁₃H₁₇BrO₉
• Molecular Weight: 397.177
• Mol file: 6919-98-8.mol

Synonyms:2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester

Chemical Property of 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester

There total 2 articles about 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy 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: 98.0%

2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester (6919-98-8) + (3aR,4S,6R,7S,7aR)-6-Benzyloxymethyl-7-hydroxy-4-phenylsulfanyl-tetrahydro-pyrano[3,4-d]oxazol-2-one (371123-29-4) → (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-((3aR,4S,6R,7S,7aR)-6-benzyloxymethyl-2-oxo-4-phenylsulfanyl-hexahydro-pyrano[3,4-d]oxazol-7-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:

With molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2003.09.058

upstream raw materials:

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

methyl D-galactopyranuronate

Downstream raw materials:

methyl 3,4-di-O-benzyl-2-O--α-L-rhamnopyranoside

methyl <3-benzoyloxy-2-methoxyestra-1,3,5(10)-trien-17β-yl>-2,3,4-tri-O-acetyl-β-D-glucopyranosidouronate

methyl <2-benzyloxy-3-methoxyestra-1,3,5(10)-trien-17β-yl>-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate

p-nitrophenyl lithocholate 3-glucuronide acetate-methyl ester