4-O-acetyl-3-O-(4-O-acetyl-6-bromo-2,6-dideoxy-2-thiophenyl-β-D-glucopyranosyl)-6-bromo-2,6-dideoxy-D-arabino-hex-1-enitol

Base Information

• Chemical Name: 4-O-acetyl-3-O-(4-O-acetyl-6-bromo-2,6-dideoxy-2-thiophenyl-β-D-glucopyranosyl)-6-bromo-2,6-dideoxy-D-arabino-hex-1-enitol
• CAS No.: 470456-74-7
• Molecular Formula: C₂₂H₂₆Br₂O₈S
• Molecular Weight: 610.318
• Mol file: 470456-74-7.mol

Synonyms:4-O-acetyl-3-O-(4-O-acetyl-6-bromo-2,6-dideoxy-2-thiophenyl-β-D-glucopyranosyl)-6-bromo-2,6-dideoxy-D-arabino-hex-1-enitol

Chemical Property of 4-O-acetyl-3-O-(4-O-acetyl-6-bromo-2,6-dideoxy-2-thiophenyl-β-D-glucopyranosyl)-6-bromo-2,6-dideoxy-D-arabino-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-acetyl-3-O-(4-O-acetyl-6-bromo-2,6-dideoxy-2-thiophenyl-β-D-glucopyranosyl)-6-bromo-2,6-dideoxy-D-arabino-hex-1-enitol

There total 1 articles about 4-O-acetyl-3-O-(4-O-acetyl-6-bromo-2,6-dideoxy-2-thiophenyl-β-D-glucopyranosyl)-6-bromo-2,6-dideoxy-D-arabino-hex-1-enitol 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:

Acetic acid (2S,3S,4S,5R,6R)-6-((2S,3S,4R)-3-acetoxy-2-bromomethyl-3,4-dihydro-2H-pyran-4-yloxy)-2-bromomethyl-4-tert-butoxy-5-phenylsulfanyl-tetrahydro-pyran-3-yl ester → 4-O-acetyl-3-O-(4-O-acetyl-6-bromo-2,6-dideoxy-2-thiophenyl-β-D-glucopyranosyl)-6-bromo-2,6-dideoxy-D-arabino-hex-1-enitol (470456-74-7)

Guidance literature:

With hydrogen fluoride; triethylamine; In acetonitrile;

DOI:10.1071/CH01199

Reference yield: 70.0%

Acetic acid (2S,3S,4S)-3-azido-6-benzenesulfinyl-2-methyl-tetrahydro-pyran-4-yl ester + 4-O-acetyl-3-O-(4-O-acetyl-6-bromo-2,6-dideoxy-2-thiophenyl-β-D-glucopyranosyl)-6-bromo-2,6-dideoxy-D-arabino-hex-1-enitol (470456-74-7) → 4-O-acetyl-3-O-[4-O-acetyl-3-O-(3-O-acetyl-4-azido-2,4,6-trideoxy-α-L-glucopyranosyl)-6-bromo-2,6-dideoxy-2-thiophenyl-β-D-glucopyranosyl]-6-bromo-2,6-dideoxy-D-arabino-hex-1-enitol (470456-75-8)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethanesulfonic acid anhydride; In various solvent(s); at -78 - -65 ℃; for 0.166667h;

DOI:10.1071/CH01199

Reference yield:

4-O-acetyl-3-O-(4-O-acetyl-6-bromo-2,6-dideoxy-2-thiophenyl-β-D-glucopyranosyl)-6-bromo-2,6-dideoxy-D-arabino-hex-1-enitol (470456-74-7) → 4-O-acetyl-3-O-[4-O-acetyl-3-O-(3-O-acetyl-4-azido-2,4,6-trideoxy-α-L-glucopyranosyl)-6-bromo-2,6-dideoxy-2-thiophenyl-β-D-glucopyranosyl]-6-bromo-2,6-dideoxy-2-thiophenyl-α-D-glucopyranose

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / 2,6-di-tert-butyl-4-methylpyridine; trifluoromethanesulfonic anhydride / various solvent(s) / 0.17 h / -78 - -65 °C

2: CH₂Cl₂ / 1 h / 0 - 20 °C

3: Ag₂CO₃; H₂O / tetrahydrofuran / 24 h

With 2,6-di-tert-butyl-4-methylpyridine; water; trifluoromethanesulfonic acid anhydride; silver carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1071/CH01199

Downstream raw materials:

4-O-acetyl-3-O-[4-O-acetyl-3-O-(3-O-acetyl-4-azido-2,4,6-trideoxy-α-L-glucopyranosyl)-6-bromo-2,6-dideoxy-2-thiophenyl-β-D-glucopyranosyl]-6-bromo-2,6-dideoxy-D-arabino-hex-1-enitol