p-tolyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranuronic acid methyl ester

Base Information

• Chemical Name: p-tolyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranuronic acid methyl ester
• CAS No.: 61025-09-0
• Molecular Formula: C₂₀H₂₄O₉S
• Molecular Weight: 440.471
• Mol file: 61025-09-0.mol

Synonyms:p-tolyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranuronic acid methyl ester

Chemical Property of p-tolyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranuronic acid methyl ester

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-tolyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranuronic acid methyl ester

There total 3 articles about p-tolyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranuronic 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: 90.0%

para-thiocresol (106-45-6) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → p-tolyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranuronic acid methyl ester (61025-09-0)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; In ethyl acetate; for 1h;

DOI:10.1002/chem.200601090

Reference yield:

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (7355-18-2) → p-tolyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranuronic acid methyl ester (61025-09-0)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen bromide; acetic acid / dichloromethane / 19 h / 20 °C

2: tetra(n-butyl)ammonium hydrogensulfate / water; ethyl acetate / 16 h / 2 - 20 °C

With hydrogen bromide; tetra(n-butyl)ammonium hydrogensulfate; acetic acid; In dichloromethane; water; ethyl acetate;

DOI:10.1016/j.carres.2021.108281

Reference yield:

α-D-glucurono-γ-lactone (14362-29-9) → p-tolyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranuronic acid methyl ester (61025-09-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide / 0 °C

1.2: 90 °C

2.1: hydrogen bromide; acetic acid / dichloromethane / 19 h / 20 °C

3.1: tetra(n-butyl)ammonium hydrogensulfate / water; ethyl acetate / 16 h / 2 - 20 °C

With hydrogen bromide; tetra(n-butyl)ammonium hydrogensulfate; acetic acid; sodium hydroxide; In dichloromethane; water; ethyl acetate;

DOI:10.1016/j.carres.2021.108281

upstream raw materials:

para-thiocresol

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

α-D-glucurono-γ-lactone

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester