2'-O-phenoxythiocarbonyl-3',5'-di-O-(tert-butyldimethylsilyl)uridine

Base Information

• Chemical Name: 2'-O-phenoxythiocarbonyl-3',5'-di-O-(tert-butyldimethylsilyl)uridine
• CAS No.: 219539-65-8
• Molecular Formula: C₂₈H₄₄N₂O₇SSi₂
• Molecular Weight: 608.904
• Mol file: 219539-65-8.mol

Synonyms:2'-O-phenoxythiocarbonyl-3',5'-di-O-(tert-butyldimethylsilyl)uridine

Chemical Property of 2'-O-phenoxythiocarbonyl-3',5'-di-O-(tert-butyldimethylsilyl)uridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-O-phenoxythiocarbonyl-3',5'-di-O-(tert-butyldimethylsilyl)uridine

There total 1 articles about 2'-O-phenoxythiocarbonyl-3',5'-di-O-(tert-butyldimethylsilyl)uridine 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: 79.0%

phenylcarbonochloridothioate (1005-56-7) + 3',5'-bis-O-(tert-butyldimethylsilyl)uridine (54925-67-6) → 2'-O-phenoxythiocarbonyl-3',5'-di-O-(tert-butyldimethylsilyl)uridine (219539-65-8)

Guidance literature:

With dmap; In acetonitrile; for 19h;

DOI:10.1021/jo061225g

Reference yield:

2'-O-phenoxythiocarbonyl-3',5'-di-O-(tert-butyldimethylsilyl)uridine (219539-65-8) → 2'-deoxy-2'-C-allyl-4'-C-benzoyloxymethyl-3'-O-(tert-butyldimethylsilyl)uridine (913972-63-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 65 percent / AIBN / toluene / 3 h / Heating

2: 75 percent / aq. AcOH / 72 h

3: Dess-Martin periodinane / CH₂Cl₂ / 2 h

4: aq. NaOH / dioxane / 17 h

5: 2.168 g / NaBH₄ / H₂O; dioxane / 5 h / 20 °C

6: 65 percent / pyridine / acetonitrile / 1.75 h / 20 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); Dess-Martin periodane; acetic acid; In 1,4-dioxane; dichloromethane; water; toluene; acetonitrile; 3: Dess-Martin oxidation;

DOI:10.1021/jo061225g

Reference yield:

2'-O-phenoxythiocarbonyl-3',5'-di-O-(tert-butyldimethylsilyl)uridine (219539-65-8) → benzoic acid 4-allyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Guidance literature:

Multi-step reaction with 7 steps

1: 65 percent / AIBN / toluene / 3 h / Heating

2: 75 percent / aq. AcOH / 72 h

3: Dess-Martin periodinane / CH₂Cl₂ / 2 h

4: aq. NaOH / dioxane / 17 h

5: 2.168 g / NaBH₄ / H₂O; dioxane / 5 h / 20 °C

6: 65 percent / pyridine / acetonitrile / 1.75 h / 20 °C

7: imidazole / dimethylformamide / 15 h

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); Dess-Martin periodane; acetic acid; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 3: Dess-Martin oxidation;

DOI:10.1021/jo061225g

upstream raw materials:

phenylcarbonochloridothioate

3',5'-bis-O-(tert-butyldimethylsilyl)uridine

Downstream raw materials:

2'-deoxy-2'-C-allyl-4'-C-benzoyloxymethyl-3'-O-(tert-butyldimethylsilyl)uridine