phenyl 2,3,6-tri-O-acetyl-4-S-acetyl-1,4-dithio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2,3,6-tri-O-acetyl-4-S-acetyl-1,4-dithio-β-D-glucopyranoside
• CAS No.: 849132-28-1
• Molecular Formula: C₂₀H₂₄O₈S₂
• Molecular Weight: 456.538
• Mol file: 849132-28-1.mol

Synonyms:phenyl 2,3,6-tri-O-acetyl-4-S-acetyl-1,4-dithio-β-D-glucopyranoside

Chemical Property of phenyl 2,3,6-tri-O-acetyl-4-S-acetyl-1,4-dithio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,3,6-tri-O-acetyl-4-S-acetyl-1,4-dithio-β-D-glucopyranoside

There total 3 articles about phenyl 2,3,6-tri-O-acetyl-4-S-acetyl-1,4-dithio-β-D-glucopyranoside 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: 88.0%

potassium thioacetate (10387-40-3) + phenyl 2,3,6-tri-O-acetyl-1-thio-4-O-trifluoromethanesulfonyl-β-D-galactoside → phenyl 2,3,6-tri-O-acetyl-4-S-acetyl-1,4-dithio-β-D-glucopyranoside (849132-28-1)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1016/j.tetasy.2004.12.004

Reference yield:

phenyl 2,3-di-O-acetyl-1-thio-β-D-galactopyranoside (208644-68-2) → phenyl 2,3,6-tri-O-acetyl-4-S-acetyl-1,4-dithio-β-D-glucopyranoside (849132-28-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / pyridine / CH₂Cl₂ / 0.5 h / -30 °C

2: pyridine / CH₂Cl₂ / 0.5 h / -30 °C

3: 88 percent / tetrahydrofuran / 16 h / 20 °C

With pyridine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2004.12.004

Reference yield:

phenyl 2,3,6-tri-O-acetyl-1-thio-β-D-galactopyranoside (881181-39-1) → phenyl 2,3,6-tri-O-acetyl-4-S-acetyl-1,4-dithio-β-D-glucopyranoside (849132-28-1)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / 0.5 h / -30 °C

2: 88 percent / tetrahydrofuran / 16 h / 20 °C

With pyridine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2004.12.004

upstream raw materials:

potassium thioacetate

phenyl 2,3-di-O-acetyl-1-thio-β-D-galactopyranoside

phenyl 2,3,6-tri-O-acetyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

Acetic acid (2S,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-5-((2R,3R,4R,5R,6S)-4,5-diacetoxy-2-acetoxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yldisulfanyl)-2-phenylsulfanyl-tetrahydro-pyran-4-yl ester