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

Base Information

• Chemical Name: 2'-O-(TERT-BUTYLDIMETHYLSILYL)-3'-DEOXY-5'-O-TRITYLURIDINE
• CAS No.: 130860-12-7
• Molecular Formula: C34H40N2O5Si
• Molecular Weight: 584.788
• Mol file: 130860-12-7.mol

Synonyms:2'-O-(TERT-BUTYLDIMETHYLSILYL)-3'-DEOXY-5'-O-TRITYLURIDINE;3'-Deoxy-2'-O-[(1,1-diMethylethyl)diMethylsilyl]-5'-O-(triphenylMethyl)uridine

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

Chemical Property:

• PSA: 82.55000
• LogP: 6.22320
• Solubility.: Dichloromethane, DMSO, Methanol, Toluene

Purity/Quality:

98%Min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 6 articles about 2'-O-(TERT-BUTYLDIMETHYLSILYL)-3'-DEOXY-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: 56.0%

2'-O-(tert-butyldimethylsilyl)-3'-O-(phenoxythiocarbonyl)-5'-O-trityluridine (130860-11-6) → 2'-O-(tert-butyldimethylsilyl)-3'-deoxy-5'-O-trityluridine (130860-12-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 110 - 120 ℃; for 3h;

DOI:10.1021/jm00106a034

Reference yield:

2'-O-(tert-butyldimethylsilyl)-5'-O-(triphenylmethyl)uridine (117136-35-3) → 2'-O-(tert-butyldimethylsilyl)-3'-deoxy-5'-O-trityluridine (130860-12-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / DMAP / acetonitrile / 20 h / Ambient temperature

2: AIBN, Bu₃SnH / toluene / 3 h / 85 °C

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; acetonitrile;

DOI:10.1080/15257779408012162

Reference yield:

5'-O-trityluridine (6554-10-5) → 2'-O-(tert-butyldimethylsilyl)-3'-deoxy-5'-O-trityluridine (130860-12-7)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: AIBN, Bu₃SnH / toluene / 3 h / 85 °C

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; acetonitrile;

DOI:10.1080/15257779408012162

upstream raw materials:

2'-O-(tert-butyldimethylsilyl)-3'-O-(phenoxythiocarbonyl)-5'-O-trityluridine

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

tert-butyldimethylsilyl chloride

5'-O-trityluridine

Downstream raw materials:

3'-deoxyuridine

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

3'-deoxycytidine

N⁴-benzoyl-3'-deoxyribicytidine

Refernces

• 1、 Lin, Tai-Shun,Yang, Jin-Hua,Liu, Mao-Chin,Shen, Zhi-Yi,Cheng, Yung-Chi,et al.. "Synthesis and Anticancer Activity of Various 3'-Deoxy Pyrimidine Nucleoside Analogues and Crystal Structure of 1-(3-Deoxy-β-D-threo-pentofuranosyl)cytosine". . p. 693 - 701. Retrieved 2007/10/02.