9-[(2-tert-butyldimethylsilyloxymethyl-2-ethynyl-1-phenylselenyl-1-cyclopropyl)methyl]adenine

Base Information

• Chemical Name: 9-[(2-tert-butyldimethylsilyloxymethyl-2-ethynyl-1-phenylselenyl-1-cyclopropyl)methyl]adenine
• CAS No.: 951793-12-7
• Molecular Formula: C₂₄H₃₁N₅OSeSi
• Molecular Weight: 512.589
• Mol file: 951793-12-7.mol

Synonyms:9-[(2-tert-butyldimethylsilyloxymethyl-2-ethynyl-1-phenylselenyl-1-cyclopropyl)methyl]adenine

Chemical Property of 9-[(2-tert-butyldimethylsilyloxymethyl-2-ethynyl-1-phenylselenyl-1-cyclopropyl)methyl]adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-[(2-tert-butyldimethylsilyloxymethyl-2-ethynyl-1-phenylselenyl-1-cyclopropyl)methyl]adenine

There total 7 articles about 9-[(2-tert-butyldimethylsilyloxymethyl-2-ethynyl-1-phenylselenyl-1-cyclopropyl)methyl]adenine 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%

1-bromomethyl-2-ethynyl-2-tert-butyldimethylsilyloxymethyl-1-phenylselenylcyclopropane (951793-24-1) + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → 9-[(2-tert-butyldimethylsilyloxymethyl-2-ethynyl-1-phenylselenyl-1-cyclopropyl)methyl]adenine (951793-12-7)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1016/j.tet.2007.06.109

Reference yield: 42.8%

C24H31N5O2SeSi (951793-14-9) → 9-[(2-tert-butyldimethylsilyloxymethyl-2-ethynyl-1-phenylselenyl-1-cyclopropyl)methyl]adenine (951793-12-7) + C18H25N5OSi (951793-16-1) + C18H25N5OSi (951793-17-2)

Guidance literature:

In toluene; at 80 ℃; for 0.333333h; Thermolysis;

DOI:10.1016/j.tet.2007.06.109

Reference yield:

ethyl 2-hydroxymethyl-1-methylenecyclopropane 2-carboxylate (951793-19-4) → 9-[(2-tert-butyldimethylsilyloxymethyl-2-ethynyl-1-phenylselenyl-1-cyclopropyl)methyl]adenine (951793-12-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 83 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

2: 82 percent / DMAP; pyridine / CH₂Cl₂ / 24 h / 20 °C

3: 83.5 percent / pyridinium chloroformate / CH₂Cl₂ / 34 h / 20 °C

4: 94.6 percent / Ph₃P / CH₂Cl₂ / 1.5 h / 0 - 20 °C

5: 89 percent / BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

6: 40.4 percent / N-bromosuccinimide / CH₂Cl₂ / 0.42 h / -20 - -10 °C

7: 83 percent / K₂CO₃ / dimethylformamide / 16 h / 20 °C

With pyridine; dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; pyridinium chloroformate; potassium carbonate; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 4: Wittig reaction;

DOI:10.1016/j.tet.2007.06.109

upstream raw materials:

1-bromomethyl-2-ethynyl-2-tert-butyldimethylsilyloxymethyl-1-phenylselenylcyclopropane

adenine

C₂₄H₃₁N₅O₂SeSi

ethyl 2-hydroxymethyl-1-methylenecyclopropane 2-carboxylate

Downstream raw materials:

C₂₄H₃₁N₅O₂SeSi