p-tolyl-3-O-acetyl-1-thio-5-O-triisopropylsilyl-2-deoxy-β-D-ribofuranoside

Base Information

• Chemical Name: p-tolyl-3-O-acetyl-1-thio-5-O-triisopropylsilyl-2-deoxy-β-D-ribofuranoside
• CAS No.: 1402737-55-6
• Molecular Formula: C₂₃H₃₈O₄SSi
• Molecular Weight: 438.704
• Mol file: 1402737-55-6.mol

Synonyms:p-tolyl-3-O-acetyl-1-thio-5-O-triisopropylsilyl-2-deoxy-β-D-ribofuranoside

Chemical Property of p-tolyl-3-O-acetyl-1-thio-5-O-triisopropylsilyl-2-deoxy-β-D-ribofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-tolyl-3-O-acetyl-1-thio-5-O-triisopropylsilyl-2-deoxy-β-D-ribofuranoside

There total 5 articles about p-tolyl-3-O-acetyl-1-thio-5-O-triisopropylsilyl-2-deoxy-β-D-ribofuranoside 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-tolyl-1-thio-5-O-triisopropylsilyl-2-deoxy-α,β-D-ribofuranoside + acetic anhydride (108-24-7) → p-tolyl-3-O-acetyl-1-thio-5-O-triisopropylsilyl-2-deoxy-α-D-ribofuranoside (1402737-56-7) + p-tolyl-3-O-acetyl-1-thio-5-O-triisopropylsilyl-2-deoxy-β-D-ribofuranoside (1402737-55-6)

Guidance literature:

With dmap; triethylamine; In acetonitrile; at 20 ℃; for 2h; Overall yield = 90 %; Overall yield = 2.04 g; stereoselective reaction;

DOI:10.1021/jo3014929 DOI:10.1021/jo3014929

Reference yield:

p-tolyl-1-thio-5-O-triisopropylsilyl-2-deoxy-D-ribofuranoside + acetic anhydride (108-24-7) → p-tolyl-3-O-acetyl-1-thio-5-O-triisopropylsilyl-2-deoxy-α-D-ribofuranoside (1402737-56-7) + p-tolyl-3-O-acetyl-1-thio-5-O-triisopropylsilyl-2-deoxy-β-D-ribofuranoside (1402737-55-6)

Guidance literature:

With dmap; triethylamine; In acetonitrile; at 20 ℃; for 2h; Overall yield = 90 %; Overall yield = 2.04 g;

DOI:10.1021/ol400930s

Reference yield:

1,3,5-tri-O-acetyl-2-deoxyribose (4594-52-9,96291-74-6,96291-75-7) → p-tolyl-3-O-acetyl-1-thio-5-O-triisopropylsilyl-2-deoxy-α-D-ribofuranoside (1402737-56-7) + p-tolyl-3-O-acetyl-1-thio-5-O-triisopropylsilyl-2-deoxy-β-D-ribofuranoside (1402737-55-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dichloromethane / 0.08 h / -78 °C

1.2: 0.33 h / -78 °C

2.1: potassium carbonate / dichloromethane; methanol / 2 h / 25 °C

3.1: 1H-imidazole / dichloromethane / 16 h / 25 °C

4.1: triethylamine; dmap / acetonitrile / 15 h / 25 °C

With 1H-imidazole; dmap; potassium carbonate; triethylamine; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/jacs.0c05180

upstream raw materials:

acetic anhydride

1,3,5-tri-O-acetyl-2-deoxyribose

para-thiocresol