6-N-benzoyl-3',5'-bis-O-tert-butyldimethylsilyladenosin-2'-yl-2-cyanoethyl N,N-diisopropylphosphoramidite

Base Information

• Chemical Name: 6-N-benzoyl-3',5'-bis-O-tert-butyldimethylsilyladenosin-2'-yl-2-cyanoethyl N,N-diisopropylphosphoramidite
• CAS No.: 171022-45-0
• Molecular Formula: C₃₈H₆₂N₇O₆PSi₂
• Molecular Weight: 800.098
• Mol file: 171022-45-0.mol

Synonyms:

Chemical Property of 6-N-benzoyl-3',5'-bis-O-tert-butyldimethylsilyladenosin-2'-yl-2-cyanoethyl N,N-diisopropylphosphoramidite

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-N-benzoyl-3',5'-bis-O-tert-butyldimethylsilyladenosin-2'-yl-2-cyanoethyl N,N-diisopropylphosphoramidite

There total 1 articles about 6-N-benzoyl-3',5'-bis-O-tert-butyldimethylsilyladenosin-2'-yl-2-cyanoethyl N,N-diisopropylphosphoramidite 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: 62.0%

6-N-benzoyl-3',5'-bis-O-tert-butyldimethylsilyladenosine (88121-45-3) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 6-N-benzoyl-3',5'-bis-O-tert-butyldimethylsilyladenosin-2'-yl-2-cyanoethyl N,N-diisopropylphosphoramidite (171022-45-0,171022-47-2)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 3h; Ambient temperature;

Reference yield:

6-N-benzoyl-3',5'-bis-O-tert-butyldimethylsilyladenosin-2'-yl-2-cyanoethyl N,N-diisopropylphosphoramidite (171022-45-0,171022-47-2) → adenosine 2'-phosphorothioate biscyclohexylamine salt

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 1H-tetrazole, 2.) S₈ / 1.) acetonitrile, room temperature, 3 h, 2.) pyridine, room temperature, 15 min

2: 1.) NH₄OH, 2.) TBAF, 3.) Amberlite IR 118 / 1.) H₂O, EtOH, 60 deg C, 20 h, 2.) THF, 10 h, 3.) H₂O

With 1H-tetrazole; sulfur; ammonium hydroxide; Amberlite IR 118; tetrabutyl ammonium fluoride;

Reference yield:

3-Hydroxypropionitrile (109-78-4) + 6-N-benzoyl-3',5'-bis-O-tert-butyldimethylsilyladenosin-2'-yl-2-cyanoethyl N,N-diisopropylphosphoramidite (171022-45-0,171022-47-2) → 6-N-benzoyl-3',5'-bis-O-(tert-butyldimethylsilyl)adenosin-2'-yl-bis-2-cyanoethylphosphorothioate

Guidance literature:

With 1H-tetrazole; sulfur; Yield given. Multistep reaction; 1.) acetonitrile, room temperature, 3 h, 2.) pyridine, room temperature, 15 min;

upstream raw materials:

6-N-benzoyl-3',5'-bis-O-tert-butyldimethylsilyladenosine

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine