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

Base Information

• Chemical Name: 3',5'-O-di-tert-butylsilyl-5-tert-butyldimethylsiloxymethyl-N⁽⁴⁾-benzoyl-2'-deoxycytidine
• CAS No.: 1292210-12-8
• Molecular Formula: C₃₁H₄₉N₃O₆Si₂
• Molecular Weight: 615.918

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

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

Chemical Property:

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

There total 11 articles about 3',5'-O-di-tert-butylsilyl-5-tert-butyldimethylsiloxymethyl-N⁽⁴⁾-benzoyl-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: 80.0%

3',5'-O-di-tert-butylsilyl-5-tert-butyldimethylsiloxymethyl-2'-deoxycytidine (1292210-11-7) + benzoyl chloride (98-88-4) → 3',5'-O-di-tert-butylsilyl-5-tert-butyldimethylsiloxymethyl-N(4)-benzoyl-2'-deoxycytidine (1292210-12-8)

Guidance literature:

With pyridine; at 20 ℃; Inert atmosphere;

DOI:10.1021/jo200566d

Reference yield:

3',5'-O-di-tert-butylsilyl-5-tert-butyldimethylsiloxymethyl-2'-deoxyuridine (1292210-07-1) → 3',5'-O-di-tert-butylsilyl-5-tert-butyldimethylsiloxymethyl-N(4)-benzoyl-2'-deoxycytidine (1292210-12-8)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine; trichlorophosphate / acetonitrile / 1.5 h / 0 °C

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

3: pyridine / 20 °C / Inert atmosphere

With pyridine; ammonium hydroxide; triethylamine; trichlorophosphate; In 1,4-dioxane; acetonitrile;

DOI:10.1021/jo200566d

Reference yield:

3',5'-O-di-tert-butylsilyl-5-iodo-2'-deoxyuridine (1292210-08-2) → 3',5'-O-di-tert-butylsilyl-5-tert-butyldimethylsiloxymethyl-N(4)-benzoyl-2'-deoxycytidine (1292210-12-8)

Guidance literature:

Multi-step reaction with 6 steps

1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tri-n-butyl-tin hydride; triphenylphosphine / tetrahydrofuran / 3 h / 70 °C / 2585.81 Torr

2: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.75 h / 0 - 20 °C / Inert atmosphere

3: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere

4: triethylamine; trichlorophosphate / acetonitrile / 1.5 h / 0 °C

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

6: pyridine / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; ammonium hydroxide; sodium tetrahydroborate; cerium(III) chloride heptahydrate; tri-n-butyl-tin hydride; triethylamine; triphenylphosphine; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; acetonitrile; 1: Stille reaction;

DOI:10.1021/jo200566d

upstream raw materials:

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

benzoyl chloride

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

3',5'-O-di-tert-butylsilyl-5-iodo-2'-deoxyuridine

Downstream raw materials:

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

5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-N⁽⁴⁾-benzoyl-2'-deoxycytidine

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

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