p-tolyl 6-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: p-tolyl 6-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside
• CAS No.: 794520-99-3
• Molecular Formula: C₁₉H₃₂O₅SSi
• Molecular Weight: 400.612
• Mol file: 794520-99-3.mol

Synonyms:p-tolyl 6-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside

Chemical Property of p-tolyl 6-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-tolyl 6-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside

There total 2 articles about p-tolyl 6-O-(tert-butyldimethylsilyl)-1-thio-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:

p-methylphenyl 1-thio-β-D-glucopyranoside (1152-39-2) + tert-butyldimethylsilyl chloride (18162-48-6) → p-tolyl 6-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside (794520-99-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1.5h;

DOI:10.1016/j.tet.2004.08.012

Reference yield:

p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (28244-94-2,28244-99-7,86782-41-4,131488-65-8) → p-tolyl 6-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside (794520-99-3)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / methanol / 2 h / 20 °C

2: 203 mg / imidazole / dimethylformamide / 1.5 h / 20 °C

With 1H-imidazole; potassium carbonate; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.08.012

Reference yield: 96.0%

acetic anhydride (108-24-7) + p-tolyl 6-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside (794520-99-3) → p-tolyl 2,3,4-O-tris(acetyl)-6-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside (794521-01-0)

Guidance literature:

With pyridine; dmap; at 60 ℃; for 4h;

DOI:10.1016/j.tet.2004.08.012

upstream raw materials:

p-methylphenyl 1-thio-β-D-glucopyranoside

tert-butyldimethylsilyl chloride

p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

Downstream raw materials:

p-tolyl 2,3,4-O-tris(acetyl)-6-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside

p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

p-tolyl 6-(tert-butyldimethylsilyloxy)-3-O-(p-toluenesulfonyl)-β-D-glucopyranoside

S-4-methylphenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside