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

Base Information

• Chemical Name: Thiophosphoric acid O-[(2R,3R,4R,5R)-2-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl] ester O',O''-bis-(2-cyano-1,1-dimethyl-ethyl) ester
• CAS No.: 176664-00-9
• Molecular Formula: C₂₆H₃₁N₄O₉PS
• Molecular Weight: 606.593
• Mol file: 176664-00-9.mol

Synonyms:

Chemical Property of Thiophosphoric acid O-[(2R,3R,4R,5R)-2-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl] ester O',O''-bis-(2-cyano-1,1-dimethyl-ethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thiophosphoric acid O-[(2R,3R,4R,5R)-2-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl] ester O',O''-bis-(2-cyano-1,1-dimethyl-ethyl) ester

There total 5 articles about Thiophosphoric acid O-[(2R,3R,4R,5R)-2-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl] ester O',O''-bis-(2-cyano-1,1-dimethyl-ethyl) ester 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:

Thiophosphoric acid O-[(4aR,6R,7R,7aR)-6-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-di-tert-butyl-tetrahydro-furo[3,2-d][1,3,2]dioxasilin-7-yl] ester O',O''-bis-(2-cyano-1,1-dimethyl-ethyl) ester (176663-99-3) → Thiophosphoric acid O-[(2R,3R,4R,5R)-2-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl] ester O',O''-bis-(2-cyano-1,1-dimethyl-ethyl) ester (176664-00-9)

Guidance literature:

With (HF)x*Py; In tetrahydrofuran; pyridine; for 0.166667h; Yield given; Ambient temperature;

DOI:10.1021/jo952073k

Reference yield:

3-hydroxy-3-methylbutyronitrile (13635-04-6) → Thiophosphoric acid O-[(2R,3R,4R,5R)-2-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl] ester O',O''-bis-(2-cyano-1,1-dimethyl-ethyl) ester (176664-00-9)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jo952073k

Reference yield:

N3-benzoyluridine (86988-30-9) → Thiophosphoric acid O-[(2R,3R,4R,5R)-2-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl] ester O',O''-bis-(2-cyano-1,1-dimethyl-ethyl) ester (176664-00-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / AgNO₃ / dimethylformamide / 0.5 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

With 1H-tetrazole; sulfur; (HF)x*Py; silver nitrate; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide;

DOI:10.1021/jo952073k

upstream raw materials:

Thiophosphoric acid O-[(4aR,6R,7R,7aR)-6-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-di-tert-butyl-tetrahydro-furo[3,2-d][1,3,2]dioxasilin-7-yl] ester O',O''-bis-(2-cyano-1,1-dimethyl-ethyl) ester

3-hydroxy-3-methylbutyronitrile

N³-benzoyluridine

N³-benzoyl-3',5'-O-(di-tert-butylsilanediyl)uridine

Downstream raw materials:

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