phenyl 4-O-acetyl-2,3-O-(2’,3’-dimethoxy-2’,3’-dimethylbutane)-1-thio-β-L-quinovopyranoside

Base Information

• Chemical Name: phenyl 4-O-acetyl-2,3-O-(2’,3’-dimethoxy-2’,3’-dimethylbutane)-1-thio-β-L-quinovopyranoside
• CAS No.: 912478-21-8
• Molecular Formula: C₂₀H₂₈O₇S
• Molecular Weight: 412.504
• Mol file: 912478-21-8.mol

Synonyms:phenyl 4-O-acetyl-2,3-O-(2’,3’-dimethoxy-2’,3’-dimethylbutane)-1-thio-β-L-quinovopyranoside

Chemical Property of phenyl 4-O-acetyl-2,3-O-(2’,3’-dimethoxy-2’,3’-dimethylbutane)-1-thio-β-L-quinovopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 4-O-acetyl-2,3-O-(2’,3’-dimethoxy-2’,3’-dimethylbutane)-1-thio-β-L-quinovopyranoside

There total 5 articles about phenyl 4-O-acetyl-2,3-O-(2’,3’-dimethoxy-2’,3’-dimethylbutane)-1-thio-β-L-quinovopyranoside 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: 64.0%

phenyl 2,3-O-(2',3'-dimethoxy-2',3'-dimethylbutane)-1-thio-β-L-fucopyranoside (912478-19-4) + tetrabutylammonium acetate (10534-59-5) → phenyl 4-O-acetyl-2,3-O-(2’,3’-dimethoxy-2’,3’-dimethylbutane)-1-thio-β-L-quinovopyranoside (912478-21-8)

Guidance literature:

phenyl 2,3-O-(2',3'-dimethoxy-2',3'-dimethylbutane)-1-thio-β-L-fucopyranoside; With trifluoromethanesulfonic acid anhydride; In pyridine; dichloromethane; at -40 ℃; for 0.5h;

tetrabutylammonium acetate; In toluene; for 24h; sonication;

DOI:10.1021/ja064619y

Reference yield:

C18H26O7S + acetic anhydride (108-24-7) → phenyl 4-O-acetyl-2,3-O-(2’,3’-dimethoxy-2’,3’-dimethylbutane)-1-thio-β-L-quinovopyranoside (912478-21-8) + phenyl 4,6-di-O-acetyl-2,3-O-(2’,3’-dimethoxy-2’,3’-dimethylbutane)-1-thio-β-L-glucopyranoside

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1002/anie.201408209

Reference yield:

C22H36O6SSi → phenyl 4-O-acetyl-2,3-O-(2’,3’-dimethoxy-2’,3’-dimethylbutane)-1-thio-β-L-quinovopyranoside (912478-21-8) + phenyl 4,6-di-O-acetyl-2,3-O-(2’,3’-dimethoxy-2’,3’-dimethylbutane)-1-thio-β-L-glucopyranoside

Guidance literature:

Multi-step reaction with 3 steps

1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; norbornene; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 120 °C / Inert atmosphere; Schlenk technique

2: potassium fluoride; urea hydrogen peroxide adduct; potassium carbonate / N,N-dimethyl-formamide / 1 h / 50 °C / Inert atmosphere

3: triethylamine; dmap / dichloromethane / 20 °C

With dmap; potassium fluoride; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin; norbornene; urea hydrogen peroxide adduct; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2: |Fleming-Tamao Oxidation;

DOI:10.1002/anie.201408209

upstream raw materials:

phenyl 2,3-O-(2',3'-dimethoxy-2',3'-dimethylbutane)-1-thio-β-L-fucopyranoside

tetrabutylammonium acetate

phenyl 2,3-O-(2',3'-dimethoxy-2',3'-dimethylbutane)-1-thio-β-L-quinovopyranoside

acetic anhydride

Downstream raw materials:

phenyl 4-azido-4-deoxy-2,3-O-(2',3'-dimethoxy-2',3'-dimethylbutane)-1-thio-β-L-fucopyranoside

phenyl 4-azido-4-deoxy-1-thio-β-L-fucopyranoside

phenyl 2,3-O-(2',3'-dimethoxy-2',3'-dimethylbutane)-1-thio-β-L-quinovopyranoside