N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine

Base Information

• Chemical Name: N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine
• CAS No.: 1277097-10-5
• Molecular Formula: C₄₁H₄₀N₄O₈
• Molecular Weight: 716.791
• Mol file: 1277097-10-5.mol

Synonyms:N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine

Chemical Property of N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine

There total 10 articles about N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine 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: 90.0%

5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine (1277097-09-2) + benzoic acid anhydride (93-97-0) → N4-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine (1277097-10-5)

Guidance literature:

In N,N-dimethyl-formamide; for 42h; chemoselective reaction;

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 (1277097-10-5)

Guidance literature:

Multi-step reaction with 4 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

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'-deoxy-5-(hydroxymethyl)uridine (5116-24-5,15425-01-1,143156-50-7) → N4-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine (1277097-10-5)

Guidance literature:

Multi-step reaction with 5 steps

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

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

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

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

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

With tetrabutylammomium bromide; ammonia; lithium carbonate; sodium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 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

Downstream raw materials:

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