N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-[N,N-diisopropyl-N-cyanoethyl]phosphoramidite

Base Information

• Chemical Name: N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-[N,N-diisopropyl-N-cyanoethyl]phosphoramidite
• CAS No.: 188411-06-5
• Molecular Formula: C₅₀H₅₇N₆O₉P
• Molecular Weight: 917.011
• Mol file: 188411-06-5.mol

Synonyms:N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-[N,N-diisopropyl-N-cyanoethyl]phosphoramidite

Chemical Property of N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-[N,N-diisopropyl-N-cyanoethyl]phosphoramidite

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: N-Benzoyl-5-((2-cyanoethoxy)methyl)-2’-deoxycytidine CEP is derived from Cyanoethyl N,N-Diisopropyl Phosphoamidochloridite (C980000), which is a protecting reagent in DNA synthesis and a phosphorylating agent.

Technology Process of N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-[N,N-diisopropyl-N-cyanoethyl]phosphoramidite

There total 10 articles about N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-[N,N-diisopropyl-N-cyanoethyl]phosphoramidite 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: 87.0%

N4-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine (1277097-10-5) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → N4-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-[N,N-diisopropyl-N-cyanoethyl]phosphoramidite (188411-06-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 1h; Inert atmosphere;

DOI:10.1016/j.bmcl.2010.12.098

Reference yield:

5-(2-cyanoethyl)hydroxymethyl-2'-deoxyuridine (188411-04-3) → N4-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-[N,N-diisopropyl-N-cyanoethyl]phosphoramidite (188411-06-5)

Guidance literature:

Multi-step reaction with 5 steps

1: lithium carbonate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C / Heating

2: tetrabutylammomium bromide; sodium carbonate / dichloromethane; water / 9 h

3: ammonia / 1,4-dioxane; water / 16 h

4: N,N-dimethyl-formamide / 42 h

5: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Inert atmosphere

With tetrabutylammomium bromide; ammonia; lithium carbonate; sodium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2010.12.098

Reference yield:

2'-deoxyuridine (951-78-0,63844-76-8) → N4-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-[N,N-diisopropyl-N-cyanoethyl]phosphoramidite (188411-06-5)

Guidance literature:

Multi-step reaction with 7 steps

1: potassium hydroxide / water / 146 h / 65 °C / pH 11 / Inert atmosphere

2: trifluoroacetic acid / 1.5 h / 100 °C / 7.5 Torr / pH 1

3: lithium carbonate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C / Heating

4: tetrabutylammomium bromide; sodium carbonate / dichloromethane; water / 9 h

5: ammonia / 1,4-dioxane; water / 16 h

6: N,N-dimethyl-formamide / 42 h

7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Inert atmosphere

With tetrabutylammomium bromide; ammonia; lithium carbonate; sodium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2010.12.098

upstream raw materials:

(MeO)2Tr-OAc

5-(2-cyanoethyl)hydroxymethyl-2'-deoxyuridine

5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxyuridine

5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine