1-(2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-2'-fluoro-4'-C-ethynyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-arabinofuranosyl)cytosine

Base Information

• Chemical Name: 1-(2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-2'-fluoro-4'-C-ethynyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-arabinofuranosyl)cytosine
• CAS No.: 1240471-20-8
• Molecular Formula: C₃₃H₄₄FN₃O₄Si₂
• Molecular Weight: 621.899
• Mol file: 1240471-20-8.mol

Synonyms:1-(2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-2'-fluoro-4'-C-ethynyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-arabinofuranosyl)cytosine

Chemical Property of 1-(2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-2'-fluoro-4'-C-ethynyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-arabinofuranosyl)cytosine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-2'-fluoro-4'-C-ethynyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-arabinofuranosyl)cytosine

There total 10 articles about 1-(2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-2'-fluoro-4'-C-ethynyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-arabinofuranosyl)cytosine 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%

1-(2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-2'-fluoro-4'-C-ethynyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-arabinofuranosyl)uracil (1240471-17-3) → 1-(2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-2'-fluoro-4'-C-ethynyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-arabinofuranosyl)cytosine (1240471-20-8)

Guidance literature:

1-(2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-2'-fluoro-4'-C-ethynyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-arabinofuranosyl)uracil; With dmap; Triphenylsilyl chloride; triethylamine; In acetonitrile; at 20 ℃; for 12h;

With ammonium hydroxide; In water; acetonitrile; at 20 ℃; for 2h;

Reference yield:

C33H42Cl2FN2O6PSi2 → 1-(2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-2'-fluoro-4'-C-ethynyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-arabinofuranosyl)cytosine (1240471-20-8)

Guidance literature:

With ammonium hydroxide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2010.05.090

Reference yield:

1-(2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-2'-fluoro-4'-C-hydroxymethyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-arabinofuranosyl)uracil (1240471-13-9,1445379-64-5) → 1-(2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-2'-fluoro-4'-C-ethynyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-arabinofuranosyl)cytosine (1240471-20-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C

2.1: 4-toluenesulfonyl azide; potassium carbonate / acetonitrile / 2 h / 20 °C

2.2: 12 h / 20 °C

3.1: dmap; triethylamine; Triphenylsilyl chloride / acetonitrile / 12 h / 20 °C

3.2: 2 h / 20 °C

With dmap; 4-toluenesulfonyl azide; Triphenylsilyl chloride; potassium carbonate; Dess-Martin periodane; triethylamine; In dichloromethane; acetonitrile;

upstream raw materials:

1-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)uracil

1-(2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-2'-fluoro-4'-C-hydroxymethyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-arabinofuranosyl)uracil

1-(2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-2'-fluoro-4'-C-ethynyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-arabinofuranosyl)uracil

1-(2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-2'-fluoro-β-D-arabinofuranosyl)uracil