2'-O-allyl-5'-O-tosyl-araU

Base Information

• Chemical Name: 2'-O-allyl-5'-O-tosyl-araU
• CAS No.: 245078-07-3
• Molecular Formula: C₁₉H₂₂N₂O₈S
• Molecular Weight: 438.458
• Mol file: 245078-07-3.mol

Synonyms:2'-O-allyl-5'-O-tosyl-araU

Chemical Property of 2'-O-allyl-5'-O-tosyl-araU

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-O-allyl-5'-O-tosyl-araU

There total 8 articles about 2'-O-allyl-5'-O-tosyl-araU 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: 89.0%

2'-O-allyl-3'-O-tert-butyldimethylsilyl-5'-O-tosyl-araU (245078-06-2) → 2'-O-allyl-5'-O-tosyl-araU (245078-07-3)

Guidance literature:

With hydrogen fluoride; at 23 ℃;

DOI:10.1021/jm9807095

Reference yield:

2,2'-Anhydrouridine (3736-77-4) → 2'-O-allyl-5'-O-tosyl-araU (245078-07-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: p-toluenesulfonic acid monohydrate / acetonitrile / 3 h / 20 °C

2.1: KOH / ethanol / 4 h / Heating

3.1: NaH / tetrahydrofuran / 0.17 h

3.2: 40 percent / tetrahydrofuran / 17 h

4.1: 63 percent / TsOH*H₂O / methanol / 20 °C

5.1: 51 percent / Et₃N / dimethylformamide / 20 h / 60 °C

6.1: 54 percent / 80 percent aq. AcOH / 6 h / 60 °C

7.1: 84 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 20 h / 4 °C

8.1: 89 percent / aq. HF / 23 °C

With dmap; potassium hydroxide; hydrogen fluoride; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Addition / 2.1: Hydrolysis / 3.1: Metallation / 3.2: Alkylation / 4.1: Deprotection / 5.1: Silylation / 6.1: Hydrolysis / 7.1: Tosylation / 8.1: Hydrolysis;

DOI:10.1021/jm9807095

Reference yield:

9-<3,5-di-O-(tetrahydropyran-2-yl)-β-D-arabinofuranosyl>uracil (157024-75-4) → 2'-O-allyl-5'-O-tosyl-araU (245078-07-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaH / tetrahydrofuran / 0.17 h

1.2: 40 percent / tetrahydrofuran / 17 h

2.1: 63 percent / TsOH*H₂O / methanol / 20 °C

3.1: 51 percent / Et₃N / dimethylformamide / 20 h / 60 °C

4.1: 54 percent / 80 percent aq. AcOH / 6 h / 60 °C

5.1: 84 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 20 h / 4 °C

6.1: 89 percent / aq. HF / 23 °C

With dmap; hydrogen fluoride; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Alkylation / 2.1: Deprotection / 3.1: Silylation / 4.1: Hydrolysis / 5.1: Tosylation / 6.1: Hydrolysis;

DOI:10.1021/jm9807095

upstream raw materials:

2'-O-allyl-3'-O-tert-butyldimethylsilyl-5'-O-tosyl-araU

2,2'-Anhydrouridine

3',5'-di-O-(tetrahydropyran-2-yl)-2,2'-O-cyclouridine

9-<3,5-di-O-(tetrahydropyran-2-yl)-β-D-arabinofuranosyl>uracil