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

Base Information

• Chemical Name: 1',2'-didehydro-2'-deoxy-3',5'-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-N⁷-triphenylphosphoranylideneadenosine
• CAS No.: 201677-02-3
• Molecular Formula: C₄₀H₅₂N₅O₃PSi₂
• Molecular Weight: 738.029
• Mol file: 201677-02-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about 1',2'-didehydro-2'-deoxy-3',5'-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-N⁷-triphenylphosphoranylideneadenosine 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: 66.0%

9-[2-deoxy-2-iodo-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-β-D-arabinofuranosyl]-9H-purin-6-N-triphenylphosphoranylideneamine (201677-00-1) → 1',2'-didehydro-2'-deoxy-3',5'-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-N7-triphenylphosphoranylideneadenosine (201677-02-3)

Guidance literature:

With DBN; In pyridine; at 20 ℃; for 24h;

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

Reference yield:

3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-adenosine (69504-03-6) → 1',2'-didehydro-2'-deoxy-3',5'-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-N7-triphenylphosphoranylideneadenosine (201677-02-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 59 percent / imidazole; iodine / toluene / 3 h / Heating

2: 66 percent / 1,5-diazobicyclo[4.3.0]non-5-ene / pyridine / 24 h / 20 °C

With 1H-imidazole; DBN; iodine; In pyridine; toluene; 1: Iodination / 2: Dehydroiodination;

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

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 1',2'-didehydro-2'-deoxy-3',5'-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-N7-triphenylphosphoranylideneadenosine (201677-02-3)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 66 percent / 1,5-diazobicyclo[4.3.0]non-5-ene / pyridine / 24 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; DBN; iodine; silver nitrate; In tetrahydrofuran; pyridine; toluene; 1: silylation / 2: Iodination / 3: Dehydroiodination;

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

upstream raw materials:

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

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

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