2'-O-bis[(2-cyano-1,1-dimethylethoxy)thiophosphoryl]-N³-benzoyl-5'-O-(4,4'-dimethoxytrityl)uridine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite)

Base Information

• Chemical Name: 2'-O-bis[(2-cyano-1,1-dimethylethoxy)thiophosphoryl]-N³-benzoyl-5'-O-(4,4'-dimethoxytrityl)uridine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite)
• CAS No.: 176664-16-7
• Molecular Formula: C₅₆H₆₆N₆O₁₂P₂S
• Molecular Weight: 1109.19
• Mol file: 176664-16-7.mol

Synonyms:2'-O-bis[(2-cyano-1,1-dimethylethoxy)thiophosphoryl]-N³-benzoyl-5'-O-(4,4'-dimethoxytrityl)uridine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite)

Chemical Property of 2'-O-bis[(2-cyano-1,1-dimethylethoxy)thiophosphoryl]-N³-benzoyl-5'-O-(4,4'-dimethoxytrityl)uridine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-O-bis[(2-cyano-1,1-dimethylethoxy)thiophosphoryl]-N³-benzoyl-5'-O-(4,4'-dimethoxytrityl)uridine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite)

There total 8 articles about 2'-O-bis[(2-cyano-1,1-dimethylethoxy)thiophosphoryl]-N³-benzoyl-5'-O-(4,4'-dimethoxytrityl)uridine 3'-(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: 84.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + Thiophosphoric acid O-{(2R,3R,4R,5R)-2-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-3-yl} ester O',O''-bis-(2-cyano-1,1-dimethyl-ethyl) ester (176663-98-2) → 2'-O-bis[(2-cyano-1,1-dimethylethoxy)thiophosphoryl]-N3-benzoyl-5'-O-(4,4'-dimethoxytrityl)uridine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite) (176664-16-7)

Guidance literature:

With triethylamine; In dichloromethane; for 1h;

DOI:10.1021/jo952073k

Reference yield:

3-hydroxy-3-methylbutyronitrile (13635-04-6) → 2'-O-bis[(2-cyano-1,1-dimethylethoxy)thiophosphoryl]-N3-benzoyl-5'-O-(4,4'-dimethoxytrityl)uridine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite) (176664-16-7)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / diethyl ether / 3.5 h / Ambient temperature

2: 1.) 1H-tetrazole, 2.) S₈ / 1.) CH₂Cl₂, room temperature, 45 min, 2.) CS₂, room temperature, 2 h

3: (HF)x*Py / tetrahydrofuran; pyridine / 0.17 h / Ambient temperature

4: 93 percent / pyridine / 4 h / Ambient temperature

5: 84 percent / Et₃N / CH₂Cl₂ / 1 h

With pyridine; 1H-tetrazole; sulfur; (HF)x*Py; triethylamine; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane;

DOI:10.1021/jo952073k

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 2'-O-bis[(2-cyano-1,1-dimethylethoxy)thiophosphoryl]-N3-benzoyl-5'-O-(4,4'-dimethoxytrityl)uridine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite) (176664-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / pyridine / 4 h / Ambient temperature

2: 84 percent / Et₃N / CH₂Cl₂ / 1 h

With pyridine; triethylamine; In dichloromethane;

DOI:10.1021/jo952073k

upstream raw materials:

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

Thiophosphoric acid O-{(2R,3R,4R,5R)-2-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-3-yl} ester O',O''-bis-(2-cyano-1,1-dimethyl-ethyl) ester

3-hydroxy-3-methylbutyronitrile

4,4'-dimethoxytrityl chloride

Downstream raw materials:

C₈₈H₈₀N₁₀O₂₁P₂S