2,3,4-tri-O-acetyl-1,5-anhydro-6-O-(4-methylphenylsulfonyl)-D-arabino-hex-1-enitol

Base Information

• Chemical Name: 2,3,4-tri-O-acetyl-1,5-anhydro-6-O-(4-methylphenylsulfonyl)-D-arabino-hex-1-enitol
• CAS No.: 69240-09-1
• Molecular Formula: C₁₉H₂₂O₁₀S
• Molecular Weight: 442.444
• Mol file: 69240-09-1.mol

Synonyms:2,3,4-tri-O-acetyl-1,5-anhydro-6-O-(4-methylphenylsulfonyl)-D-arabino-hex-1-enitol

Chemical Property of 2,3,4-tri-O-acetyl-1,5-anhydro-6-O-(4-methylphenylsulfonyl)-D-arabino-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4-tri-O-acetyl-1,5-anhydro-6-O-(4-methylphenylsulfonyl)-D-arabino-hex-1-enitol

There total 3 articles about 2,3,4-tri-O-acetyl-1,5-anhydro-6-O-(4-methylphenylsulfonyl)-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: 72.0%

Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-6-bromo-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester (59202-80-1) → 2,3,4-tri-O-acetyl-1,5-anhydro-6-O-(4-methylphenylsulfonyl)-D-arabino-hex-1-enitol (69240-09-1)

Guidance literature:

With tellurium; sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1071/CH04277

Reference yield:

methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside (23661-33-8) → 2,3,4-tri-O-acetyl-1,5-anhydro-6-O-(4-methylphenylsulfonyl)-D-arabino-hex-1-enitol (69240-09-1)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂SO₄

2: hydrogen bromide; acetic acid / CH₂Cl₂ / 0.75 h

3: 72 percent / sodium hydride; tellurium / dimethylformamide / 1 h / 20 °C

With tellurium; sulfuric acid; hydrogen bromide; sodium hydride; acetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1071/CH04277

Reference yield:

1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose (20113-43-3) → 2,3,4-tri-O-acetyl-1,5-anhydro-6-O-(4-methylphenylsulfonyl)-D-arabino-hex-1-enitol (69240-09-1)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen bromide; acetic acid / CH₂Cl₂ / 0.75 h

2: 72 percent / sodium hydride; tellurium / dimethylformamide / 1 h / 20 °C

With tellurium; hydrogen bromide; sodium hydride; acetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1071/CH04277

upstream raw materials:

Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-6-bromo-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside

1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose

Downstream raw materials:

Acetic acid (2S,3R,5S,6R)-5-acetoxy-2-[(1S,2R,4R)-2,4-bis-(toluene-4-sulfonyloxy)-cyclohexyloxy]-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester