5'-O-(p-monomethoxytrityl)-2'-O-phenoxythiocarbonyl-3'-deoxy-3'-C-(E-carbethoxymethylidene)-2',3'-secoribothymidine

Base Information

• Chemical Name: 5'-O-(p-monomethoxytrityl)-2'-O-phenoxythiocarbonyl-3'-deoxy-3'-C-(E-carbethoxymethylidene)-2',3'-secoribothymidine
• CAS No.: 159312-22-8
• Molecular Formula: C₄₁H₄₀N₂O₉S
• Molecular Weight: 736.843
• Mol file: 159312-22-8.mol

Synonyms:5'-O-(p-monomethoxytrityl)-2'-O-phenoxythiocarbonyl-3'-deoxy-3'-C-(E-carbethoxymethylidene)-2',3'-secoribothymidine

Chemical Property of 5'-O-(p-monomethoxytrityl)-2'-O-phenoxythiocarbonyl-3'-deoxy-3'-C-(E-carbethoxymethylidene)-2',3'-secoribothymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(p-monomethoxytrityl)-2'-O-phenoxythiocarbonyl-3'-deoxy-3'-C-(E-carbethoxymethylidene)-2',3'-secoribothymidine

There total 7 articles about 5'-O-(p-monomethoxytrityl)-2'-O-phenoxythiocarbonyl-3'-deoxy-3'-C-(E-carbethoxymethylidene)-2',3'-secoribothymidine 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: 86.0%

5'-O-(p-monomethoxytrityl)-3'-deoxy-3'-C-(E-carbethoxymethylidene)-2',3'-secoribothymidine (159312-21-7) + phenylcarbonochloridothioate (1005-56-7) → 5'-O-(p-monomethoxytrityl)-2'-O-phenoxythiocarbonyl-3'-deoxy-3'-C-(E-carbethoxymethylidene)-2',3'-secoribothymidine (159312-22-8)

Guidance literature:

With pyridine; dmap; In acetonitrile; for 0.5h;

DOI:10.1016/S0040-4020(01)90437-5

Reference yield:

5'-O-(p-monomethoxytrityl)-2',3'-secoribothymidine (159312-11-5) → 5'-O-(p-monomethoxytrityl)-2'-O-phenoxythiocarbonyl-3'-deoxy-3'-C-(E-carbethoxymethylidene)-2',3'-secoribothymidine (159312-22-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 23 percent / pyridine / Ambient temperature

2: DCC, dichloroacetic acid / dimethylsulfoxide / 2 h

3: tetrahydrofuran

4: 84 percent / NH₄F / methanol

5: 86 percent / DMAP, pyridine / acetonitrile / 0.5 h

With pyridine; dichloro-acetic acid; dmap; ammonium fluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dimethyl sulfoxide; acetonitrile;

DOI:10.1016/S0040-4020(01)90437-5

Reference yield:

(R)-3-[(4-Methoxy-phenyl)-diphenyl-methoxy]-2-[(R)-1-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-oxo-ethoxy]-propionaldehyde → 5'-O-(p-monomethoxytrityl)-2'-O-phenoxythiocarbonyl-3'-deoxy-3'-C-(E-carbethoxymethylidene)-2',3'-secoribothymidine (159312-22-8)

Guidance literature:

Multi-step reaction with 6 steps

1: NaBH₄ / ethanol

2: 23 percent / pyridine / Ambient temperature

3: DCC, dichloroacetic acid / dimethylsulfoxide / 2 h

4: tetrahydrofuran

5: 84 percent / NH₄F / methanol

6: 86 percent / DMAP, pyridine / acetonitrile / 0.5 h

With pyridine; dichloro-acetic acid; dmap; ammonium fluoride; sodium tetrahydroborate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; ethanol; dimethyl sulfoxide; acetonitrile;

DOI:10.1016/S0040-4020(01)90437-5

upstream raw materials:

5'-O-(p-monomethoxytrityl)-3'-deoxy-3'-C-(E-carbethoxymethylidene)-2',3'-secoribothymidine

phenylcarbonochloridothioate

5'-O-(p-monomethoxytrityl)-2',3'-secoribothymidine

5'-O-(p-monomethoxytrityl)-2'-O-(t-butyldimethylsilyl)-2',3'-secoribothymidine

Downstream raw materials:

5'-O-(p-monomethoxytrityl)-2',3'-dideoxy-3'-C-carbethoxymethylene-ribothymidine