3',5'-Bis-O-(tert-butyldimethylsilyl)-2’-deoxyuridine

Base Information

• Chemical Name: 3',5'-Bis-O-(tert-butyldimethylsilyl)-2’-deoxyuridine
• CAS No.: 64911-18-8
• Molecular Formula: C21H40N2O5Si2
• Molecular Weight: 456.73
• Mol file: 64911-18-8.mol

Synonyms:3',5'-Bis-O-(tert-butyldimethylsilyl)-2’-deoxyuridine;2'-Deoxy-3',5'-bis-O-[(1,1-diMethylethyl)diMethylsilyl]uridine

Chemical Property of 3',5'-Bis-O-(tert-butyldimethylsilyl)-2’-deoxyuridine

Chemical Property:

• PSA: 82.81000
• Density: 1.065g/cm³
• LogP: 4.64860
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

98%Min ^*data from raw suppliers

3'',5''-Bis-O-(tert-butyldimethylsilyl)-2’-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3',5'-Bis-O-(tert-butyldimethylsilyl)-2’-deoxyuridine

There total 4 articles about 3',5'-Bis-O-(tert-butyldimethylsilyl)-2’-deoxyuridine 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: 64.0%

diphenyl ditelluride (32294-60-3) + 2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-iodouridine (148134-86-5) → 3',5'-di-O-tert-butyldimethylsilyl-2'-deoxy-5-phenyltelluro-uridine (1256466-64-4) + 3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine (64911-18-8)

Guidance literature:

2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-iodouridine; With hydrogen; sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

diphenyl ditelluride; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.58333h;

Reference yield: 36.0%

1-((2R,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (76223-04-6) → 2'-deoxyuridine (951-78-0,63844-76-8) + 3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine (64911-18-8) + 1-((2R,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (76223-05-7) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6)

Guidance literature:

With copper(II) sulfate; In xylene; Heating;

DOI:10.1080/15257770802257846

Reference yield:

methyl-d3-magnesium iodide (41251-37-0) + 2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-iodouridine (148134-86-5) → 5-(trideuteromethyl)-3′,5′-(tert-butyl-dimethylsilyl)-2′-deoxyuridine (1280736-10-8) + 3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine (64911-18-8)

Guidance literature:

methyl-d3-magnesium iodide; 2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-iodouridine; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.5h;

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(I) bromide; In tetrahydrofuran; diethyl ether; at 20 ℃;

DOI:10.1021/ja403229y

upstream raw materials:

1-((2R,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

diphenyl ditelluride

2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-iodouridine

5-Iodo-2'-deoxyuridine

Downstream raw materials:

5-Benzylsulfanyl-1-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

5-(p-cyanobenzoyl)-2'-deoxyuridine

4-{1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonyl}-benzonitrile

(benzyloxy)(tert-butyl)dimethylsilane