N⁶-methyl-2-(2-phenylethynyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine

Base Information

• Chemical Name: N⁶-methyl-2-(2-phenylethynyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine
• CAS No.: 691409-49-1
• Molecular Formula: C₃₁H₄₇N₅O₃Si₂
• Molecular Weight: 593.917

Synonyms:N⁶-methyl-2-(2-phenylethynyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine

Chemical Property of N⁶-methyl-2-(2-phenylethynyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶-methyl-2-(2-phenylethynyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine

There total 3 articles about N⁶-methyl-2-(2-phenylethynyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine 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: 85.0%

2-iodo-N6-methyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine (691409-46-8) + phenylacetylene (536-74-3) → N6-methyl-2-(2-phenylethynyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine (691409-49-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20 ℃; for 3h;

DOI:10.1016/j.bmc.2003.12.041

Reference yield:

9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-6-chloro-2-tributylstannanyl-9H-purine → N6-methyl-2-(2-phenylethynyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine (691409-49-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.17 g / iodine / tetrahydrofuran / 4 h / 20 °C

2: 84 percent / tetrahydrofuran; ethanol / 16 h / 20 °C

3: 85 percent / Et₃N; (PPh₃)2PdCl₂; CuI / 3 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; iodine; triethylamine; In tetrahydrofuran; ethanol; 3: Sonogashira reaction;

DOI:10.1016/j.bmc.2003.12.041

Reference yield:

9-[3',5'-bis-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-erythro-pentofuranosyl]-6-chloro-2-iodopurine (133519-48-9) → N6-methyl-2-(2-phenylethynyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine (691409-49-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / tetrahydrofuran; ethanol / 16 h / 20 °C

2: 85 percent / Et₃N; (PPh₃)2PdCl₂; CuI / 3 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; ethanol; 2: Sonogashira reaction;

DOI:10.1016/j.bmc.2003.12.041

upstream raw materials:

2-iodo-N⁶-methyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine

phenylacetylene

9-[3',5'-bis-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-erythro-pentofuranosyl]-6-chloro-2-iodopurine

Downstream raw materials:

N⁶-methyl-2-(2-phenylethynyl)-2'-deoxyadenosine-3',5'-bis(dibenzylphosphate)

N⁶-methyl-2-(2-phenylethynyl)-2'-deoxyadenosine

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