5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-N⁽⁴⁾-benzoyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-N⁽⁴⁾-benzoyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
• CAS No.: 1292210-18-4
• Molecular Formula: C₅₃H₆₈N₅O₉PSi
• Molecular Weight: 978.21

Synonyms:5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-N⁽⁴⁾-benzoyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Chemical Property of 5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-N⁽⁴⁾-benzoyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Chemical Property:

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Technology Process of 5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-N⁽⁴⁾-benzoyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

There total 13 articles about 5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-N⁽⁴⁾-benzoyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)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%

5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-N(4)-benzoyl-2'-deoxycytidine (1292210-14-0) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-N(4)-benzoyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite (1292210-18-4)

Guidance literature:

With 1-methyl-1H-imidazole; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo200566d

Reference yield:

C26H45N5O5Si2 → 5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-N(4)-benzoyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite (1292210-18-4)

Guidance literature:

Multi-step reaction with 5 steps

1: ammonium hydroxide / 1,4-dioxane / 1 h / 0 °C

2: pyridine / 20 °C / Inert atmosphere

3: pyridine; hydrogen fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

4: pyridine / 20 °C / Inert atmosphere

5: 1-methyl-1H-imidazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With pyridine; 1-methyl-1H-imidazole; ammonium hydroxide; hydrogen fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1021/jo200566d

Reference yield:

3',5'-O-di-tert-butylsilyl-5-tert-butyldimethylsiloxymethyl-2'-deoxycytidine (1292210-11-7) → 5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-N(4)-benzoyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite (1292210-18-4)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 20 °C / Inert atmosphere

2: pyridine; hydrogen fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3: pyridine / 20 °C / Inert atmosphere

4: 1-methyl-1H-imidazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With pyridine; 1-methyl-1H-imidazole; hydrogen fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo200566d

upstream raw materials:

3',5'-O-di-tert-butylsilyl-5-tert-butyldimethylsiloxymethyl-2'-deoxycytidine

3',5'-O-di-tert-butylsilyl-5-tert-butyldimethylsiloxymethyl-N⁽⁴⁾-benzoyl-2'-deoxycytidine

5-tert-butyldimethylsiloxymethyl-N₄-benzoyl-2'-deoxycytidine

4,4'-dimethoxytrityl chloride

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