5'-O-(4,4'-dimethoxytrityl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)phosphinyl]-2'-O-[4-(N-dichloroacetyl-N-methylamino)benzyloxy]methyluridine

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)phosphinyl]-2'-O-[4-(N-dichloroacetyl-N-methylamino)benzyloxy]methyluridine
• CAS No.: 1020100-95-1
• Molecular Formula: C₅₀H₅₈Cl₂N₅O₁₁P
• Molecular Weight: 1006.92
• Mol file: 1020100-95-1.mol

Synonyms:5'-O-(4,4'-dimethoxytrityl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)phosphinyl]-2'-O-[4-(N-dichloroacetyl-N-methylamino)benzyloxy]methyluridine

Chemical Property of 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)phosphinyl]-2'-O-[4-(N-dichloroacetyl-N-methylamino)benzyloxy]methyluridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)phosphinyl]-2'-O-[4-(N-dichloroacetyl-N-methylamino)benzyloxy]methyluridine

There total 11 articles about 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)phosphinyl]-2'-O-[4-(N-dichloroacetyl-N-methylamino)benzyloxy]methyluridine 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:

5'-O-(4,4'-dimethoxytrityl)-2'-O-[[[4-[N-(dichloroacetyl)-N-methylamino]benzyl]oxy]methyl]uridine (1020100-92-8) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)phosphinyl]-2'-O-[4-(N-dichloroacetyl-N-methylamino)benzyloxy]methyluridine (1020100-95-1)

Guidance literature:

With triethylamine; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1021/ol0629824

Reference yield:

3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-[[[4-[N-(dichloroacetyl)-N-methylamino]benzyl]oxy]methyl]uridine (1020100-86-0) → 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)phosphinyl]-2'-O-[4-(N-dichloroacetyl-N-methylamino)benzyloxy]methyluridine (1020100-95-1)

Guidance literature:

Multi-step reaction with 3 steps

1: ammonium fluoride / methanol / 16 h / 25 °C

2: pyridine / 2 h / 25 °C

3: triethylamine / CH₂Cl₂ / 2 h / 25 °C

With pyridine; ammonium fluoride; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ol0629824

Reference yield:

C11H19NOSi → 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)phosphinyl]-2'-O-[4-(N-dichloroacetyl-N-methylamino)benzyloxy]methyluridine (1020100-95-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: CH₂Cl₂ / 2 h / 25 °C

1.2: H₂O / CH₂Cl₂; methanol / 1 h / 25 °C

2.1: N-iodosuccinimide; trifluoromethanesulfonic acid / 1,2-dichloro-ethane; diethyl ether / 0 °C

3.1: ammonium fluoride / methanol / 16 h / 25 °C

4.1: pyridine / 2 h / 25 °C

5.1: triethylamine / CH₂Cl₂ / 2 h / 25 °C

With pyridine; N-iodo-succinimide; ammonium fluoride; trifluorormethanesulfonic acid; triethylamine; In methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/ol0629824

upstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-2'-O-[[[4-[N-(dichloroacetyl)-N-methylamino]benzyl]oxy]methyl]uridine

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

3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-[[[4-[N-(dichloroacetyl)-N-methylamino]benzyl]oxy]methyl]uridine

2'-O-[[[4-[N-(dichloroacetyl)-N-methylamino]benzyl]oxy]methyl]uridine

Refernces

• 1、 Cieslak, Jacek,Kauffman, Jon S.,Kolodziejski, Michelle J.,Lloyd, John R.,Beaucage, Serge L.. "Assessment of 4-nitrogenated benzyloxymethyl groups for 2′-Hydroxyl protection in solid-phase RNA synthesis". . p. 671 - 674. Retrieved 2008/02/05.