O4-Chlorophenyl-U CEP

Base Information

• Chemical Name: O4-Chlorophenyl-U CEP
• CAS No.: 220382-28-5
• Molecular Formula: C51H64ClN4O9PSi
• Molecular Weight: 971.599
• Mol file: 220382-28-5.mol

Synonyms:O4-CHLOROPHENYL-U CEP;2-O-tert-Butyldimethylsilyl-O4-(4-chlorophenyl)-5-O-DMT-uridine 3-CE-phosphoramidite

Chemical Property of O4-Chlorophenyl-U CEP

Chemical Property:

• PSA: 149.35000
• LogP: 11.66390

Purity/Quality:

98%Min ^*data from raw suppliers

2'-O-tert-Butyldimethylsilyl-O4-(4-chlorophenyl)-5'-O-DMT-uridine 3'-CE-phosphoramidite ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of O4-Chlorophenyl-U CEP

There total 8 articles about O4-Chlorophenyl-U CEP 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: 81.8%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-4-O-(4-chlorophenyl)uridine → 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphino]-2'-O-(tert-butyldimethylsilyl)-4-O-(4-chlorophenyl)uridine (220382-28-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 7h;

DOI:10.1021/ja962858n

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphino]-2'-O-(tert-butyldimethylsilyl)-4-O-(4-chlorophenyl)uridine (220382-28-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 73.8 percent / 4-(dimethylamino)pyridine; triethylamine / pyridine / 8 h / 0 - 20 °C

2: 26.3 percent / triethylamine; AgNO₃ / tetrahydrofuran / 4 h

3: 81.8 percent / N,N-diisopropylethylamine / tetrahydrofuran / 7 h / 20 °C

With dmap; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; 1: Etherification / 2: silylation / 3: phosphitylation;

DOI:10.1021/ja962858n

Reference yield:

uridine (58-96-8) → 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphino]-2'-O-(tert-butyldimethylsilyl)-4-O-(4-chlorophenyl)uridine (220382-28-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 99.6 percent / imidazole / dimethylformamide / 6.17 h / 0 - 20 °C

2: 86.3 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 9 h / 0 - 20 °C

3: 95.5 percent / trimethylamine; triethylamine / CH₂Cl₂ / 6 h / 0 - 20 °C

4: 77.8 percent / water; glacial acetic acid / tetrahydrofuran / 13 h / 20 °C

5: 73.8 percent / 4-(dimethylamino)pyridine; triethylamine / pyridine / 8 h / 0 - 20 °C

6: 26.3 percent / triethylamine; AgNO₃ / tetrahydrofuran / 4 h

7: 81.8 percent / N,N-diisopropylethylamine / tetrahydrofuran / 7 h / 20 °C

With 1H-imidazole; dmap; water; silver nitrate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; trimethylamine; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; 1: silylation / 2: Esterification / 3: Substitution / 4: Hydrolysis / 5: Etherification / 6: silylation / 7: phosphitylation;

DOI:10.1021/ja962858n

upstream raw materials:

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

4,4'-dimethoxytrityl chloride

uridine

4-O-(4-chlorophenyl)uridine

Refernces