5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2'-phenylthiouridine

Base Information

• Chemical Name: 5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2'-phenylthiouridine
• CAS No.: 475571-78-9
• Molecular Formula: C₂₁H₃₀N₂O₅SSi
• Molecular Weight: 450.631
• Mol file: 475571-78-9.mol

Synonyms:5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2'-phenylthiouridine

Chemical Property of 5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2'-phenylthiouridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2'-phenylthiouridine

There total 1 articles about 5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2'-phenylthiouridine 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: 100.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 2'-deoxy-2'-phenylthiouridine (83087-95-0) → 5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2'-phenylthiouridine (475571-78-9)

Guidance literature:

With pyridine; at 20 ℃; for 15h;

DOI:10.1081/NCN-120006826

Reference yield: 80.0%

methanesulfonyl chloride (124-63-0) + 5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2'-phenylthiouridine (475571-78-9) → 5'-O-(tert-butyldimethylsilyl)-2'-deoxy-3'-O-methanesulfonyl-2'-phenylthiouridine (475571-79-0)

Guidance literature:

With pyridine; at 20 ℃; for 12h;

DOI:10.1081/NCN-120006826

Reference yield:

5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2'-phenylthiouridine (475571-78-9) → 5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxy-2'-phenyluridine

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / pyridine / 12 h / 20 °C

2.1: 100 percent / DBN / acetonitrile / 2 h / Heating

3.1: 81 percent / m-CPBA / CH₂Cl₂ / 0.5 h / -40 °C

4.1: NaH; EtMgBr / tetrahydrofuran / 0.33 h / -70 °C

4.2: Bu₃SnCl / tetrahydrofuran / 1 h / 20 °C

4.3: 40 mg / CuI / Pd(PPh₃)4 / dimethylformamide / 20 h / 20 °C

With pyridine; 2,6-dichloro-benzonitrile; ethylmagnesium bromide; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; acetonitrile; 4.3: Stille coupling;

DOI:10.1081/NCN-120006826

upstream raw materials:

tert-butyldimethylsilyl chloride

2'-deoxy-2'-phenylthiouridine

Downstream raw materials:

5'-O-(tert-butyldimethylsilyl)-2'-deoxy-3'-O-methanesulfonyl-2'-phenylthiouridine

5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxy-2'-phenylthiouridine

2'-benzenesulfinyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxyuridine

2'-benzenesulfonyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxyuridine