2'-O-(TERT-BUTYLDIMETHYLSILYL)-3'-O-(PHENOXYTHIONCARBONYL)-5'-O-TRITYLURIDINE

Base Information

• Chemical Name: 2'-O-(TERT-BUTYLDIMETHYLSILYL)-3'-O-(PHENOXYTHIONCARBONYL)-5'-O-TRITYLURIDINE
• CAS No.: 130860-11-6
• Molecular Formula: C41H44N2O7SSi
• Molecular Weight: 736.961
• Mol file: 130860-11-6.mol

Synonyms:2'-O-(TERT-BUTYLDIMETHYLSILYL)-3'-O-(PHENOXYTHIONCARBONYL)-5'-O-TRITYLURIDINE;2'-O-[(1,1-DiMethylethyl)diMethylsilyl]-5'-O-(triphenylMethyl)uridine 3'-(O-Phenyl carbonothioate)

Chemical Property of 2'-O-(TERT-BUTYLDIMETHYLSILYL)-3'-O-(PHENOXYTHIONCARBONYL)-5'-O-TRITYLURIDINE

Chemical Property:

• Melting Point: 104-108°C
• PSA: 133.10000
• Density: 1.272g/cm³
• LogP: 7.58220
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

2’-O-(tert-Butyldimethylsilyl)-3’-O-(phenoxythioncarbonyl)-5’-O-trityluridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A protected potential anti-cancer and anti-viral agent

Technology Process of 2'-O-(TERT-BUTYLDIMETHYLSILYL)-3'-O-(PHENOXYTHIONCARBONYL)-5'-O-TRITYLURIDINE

There total 5 articles about 2'-O-(TERT-BUTYLDIMETHYLSILYL)-3'-O-(PHENOXYTHIONCARBONYL)-5'-O-TRITYLURIDINE 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: 83.0%

2'-O-(tert-butyldimethylsilyl)-5'-O-(triphenylmethyl)uridine (117136-35-3) + phenylcarbonochloridothioate (1005-56-7) → 2'-O-(tert-butyldimethylsilyl)-3'-O-(phenoxythiocarbonyl)-5'-O-trityluridine (130860-11-6)

Guidance literature:

With dmap; In acetonitrile; for 65h; Ambient temperature;

DOI:10.1021/jm00106a034

Reference yield:

5'-O-trityluridine (6554-10-5) → 2'-O-(tert-butyldimethylsilyl)-3'-O-(phenoxythiocarbonyl)-5'-O-trityluridine (130860-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / DBU / acetonitrile / 15 h / Ambient temperature

2: 71 percent / DMAP / acetonitrile / 20 h / Ambient temperature

With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile;

DOI:10.1080/15257779408012162

Reference yield:

trityl chloride (76-83-5) → 2'-O-(tert-butyldimethylsilyl)-3'-O-(phenoxythiocarbonyl)-5'-O-trityluridine (130860-11-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / pyridine / 1.) RT, overnight, 2.) 100 deg C, 4 h

2: 57 percent / AgNO₃, pyridine / tetrahydrofuran / 72 h / Ambient temperature

3: 83 percent / 4-(dimethylamino)pyridine / acetonitrile / 65 h / Ambient temperature

With pyridine; dmap; silver nitrate; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jm00106a034

upstream raw materials:

2'-O-(tert-butyldimethylsilyl)-5'-O-(triphenylmethyl)uridine

phenylcarbonochloridothioate

tert-butyldimethylsilyl chloride

5'-O-trityluridine

Downstream raw materials:

3'-deoxyuridine

5'-O-trityl-3'-deoxyuridine

N⁴-benzoyl-5'-O-dimethoxytrityl-3'-deoxyribicytidine

3'-deoxycytidine

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