9-[2-deoxy-2-iodo-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-β-D-arabinofuranosyl]-9H-purin-6-N-triphenylphosphoranylideneamine

Base Information

• Chemical Name: 9-[2-deoxy-2-iodo-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-β-D-arabinofuranosyl]-9H-purin-6-N-triphenylphosphoranylideneamine
• CAS No.: 201677-00-1
• Molecular Formula: C₄₀H₅₃IN₅O₃PSi₂
• Molecular Weight: 865.942
• Mol file: 201677-00-1.mol

Synonyms:9-[2-deoxy-2-iodo-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-β-D-arabinofuranosyl]-9H-purin-6-N-triphenylphosphoranylideneamine

Chemical Property of 9-[2-deoxy-2-iodo-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-β-D-arabinofuranosyl]-9H-purin-6-N-triphenylphosphoranylideneamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-[2-deoxy-2-iodo-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-β-D-arabinofuranosyl]-9H-purin-6-N-triphenylphosphoranylideneamine

There total 4 articles about 9-[2-deoxy-2-iodo-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-β-D-arabinofuranosyl]-9H-purin-6-N-triphenylphosphoranylideneamine 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: 59.0%

3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-adenosine (69504-03-6) + triphenylphosphine (603-35-0) → 9-[2-deoxy-2-iodo-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-β-D-arabinofuranosyl]-9H-purin-6-N-triphenylphosphoranylideneamine (201677-00-1)

Guidance literature:

With 1H-imidazole; iodine; In toluene; for 3h; Heating;

DOI:10.1016/S0040-4020(97)10317-9

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 9-[2-deoxy-2-iodo-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-β-D-arabinofuranosyl]-9H-purin-6-N-triphenylphosphoranylideneamine (201677-00-1)

Guidance literature:

Multi-step reaction with 2 steps

1: AgNO₃; DABCO / tetrahydrofuran / 48 h / 20 °C

2: 59 percent / imidazole; iodine / toluene / 3 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; iodine; silver nitrate; In tetrahydrofuran; toluene; 1: silylation / 2: Iodination;

DOI:10.1016/S0040-4020(97)10317-9

Reference yield:

9-[2-deoxy-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-1-C-(2,2-dimethyl-1-oxopropoxy)-2-iodo-β-D-arabinofuranosyl]-9H-purin-6-amine (201677-07-8) → 9-[2-deoxy-2-iodo-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-β-D-arabinofuranosyl]-9H-purin-6-N-triphenylphosphoranylideneamine (201677-00-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: AIBN; Bu₃SnH / benzene / 0.5 h / 80 °C

1.2: KOH / ethanol / 1 h / Heating

2.1: AgNO₃; DABCO / tetrahydrofuran / 48 h / 20 °C

3.1: 59 percent / imidazole; iodine / toluene / 3 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; silver nitrate; In tetrahydrofuran; toluene; benzene; 1.1: Reduction / 1.2: Hydrolysis / 2.1: silylation / 3.1: Iodination;

DOI:10.1016/S0040-4020(97)10317-9

upstream raw materials:

3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-adenosine

triphenylphosphine

tert-butyldimethylsilyl chloride

9-[2-deoxy-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-1-C-(2,2-dimethyl-1-oxopropoxy)-2-iodo-β-D-arabinofuranosyl]-9H-purin-6-amine

Downstream raw materials:

1',2'-didehydro-2'-deoxy-3',5'-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-N⁷-triphenylphosphoranylideneadenosine