3'-(N,N-diisopropylmethylphosphonamidite)-5'-(4,4'-dimethoxytrityl)-N-benzoyl-5-([D₃]methyl)-2'-deoxycytidine

Base Information

• Chemical Name: 3'-(N,N-diisopropylmethylphosphonamidite)-5'-(4,4'-dimethoxytrityl)-N-benzoyl-5-([D₃]methyl)-2'-deoxycytidine
• CAS No.: 1280736-16-4
• Molecular Formula: C₄₅H₅₃N₄O₈P
• Molecular Weight: 811.888

Synonyms:3'-(N,N-diisopropylmethylphosphonamidite)-5'-(4,4'-dimethoxytrityl)-N-benzoyl-5-([D₃]methyl)-2'-deoxycytidine

Chemical Property of 3'-(N,N-diisopropylmethylphosphonamidite)-5'-(4,4'-dimethoxytrityl)-N-benzoyl-5-([D₃]methyl)-2'-deoxycytidine

Chemical Property:

Purity/Quality:

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Technology Process of 3'-(N,N-diisopropylmethylphosphonamidite)-5'-(4,4'-dimethoxytrityl)-N-benzoyl-5-([D₃]methyl)-2'-deoxycytidine

There total 7 articles about 3'-(N,N-diisopropylmethylphosphonamidite)-5'-(4,4'-dimethoxytrityl)-N-benzoyl-5-([D₃]methyl)-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: 100.0%

5'-(4,4'-dimethoxytrityl)-N-benzoyl-5-([D3]methyl)-2'-deoxycytidine (1280736-15-3) + N,N-diisopropylmethylphosphonamidic chloride (86030-43-5) → 3'-(N,N-diisopropylmethylphosphonamidite)-5'-(4,4'-dimethoxytrityl)-N-benzoyl-5-([D3]methyl)-2'-deoxycytidine (1280736-16-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 1.5h;

DOI:10.1002/chem.201001884

Reference yield:

5-(trideuteromethyl)-3′,5′-(tert-butyl-dimethylsilyl)-2′-deoxyuridine (1280736-10-8) → 3'-(N,N-diisopropylmethylphosphonamidite)-5'-(4,4'-dimethoxytrityl)-N-benzoyl-5-([D3]methyl)-2'-deoxycytidine (1280736-16-4)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine; trichlorophosphate / acetonitrile / 0 °C

2: ammonium-d₄ deuteroxide / acetonitrile / 4 h / 20 °C

3: dmap / dichloromethane / 20 °C

4: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 20 °C

5: pyridine / 2.5 h / 20 °C

6: N-ethyl-N,N-diisopropylamine / acetonitrile / 1.5 h / 20 °C

With pyridine; dmap; ammonium-d₄ deuteroxide; triethylamine tris(hydrogen fluoride); triethylamine; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/chem.201001884

Reference yield:

3',5'-O-bis(tert-butyldimethylsilyl)-5-([D3]methyl)-2'-deoxycytidine (1245724-75-7) → 3'-(N,N-diisopropylmethylphosphonamidite)-5'-(4,4'-dimethoxytrityl)-N-benzoyl-5-([D3]methyl)-2'-deoxycytidine (1280736-16-4)

Guidance literature:

Multi-step reaction with 4 steps

1: dmap / dichloromethane / 20 °C

2: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 20 °C

3: pyridine / 2.5 h / 20 °C

4: N-ethyl-N,N-diisopropylamine / acetonitrile / 1.5 h / 20 °C

With pyridine; dmap; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/chem.201001884

upstream raw materials:

3',5'-O-bis(tert-butyldimethylsilyl)-5-([D₃]methyl)-2'-deoxycytidine

4-(N-1-triazolyl)-3',5'-O-bis(tert-butyldimethylsilyl)-5-([D₃]methyl)-2'-deoxyuridine

5-(trideuteromethyl)-3′,5′-(tert-butyl-dimethylsilyl)-2′-deoxyuridine

3',5'-O-bis(tert-butyldimethylsilyl)-N-benzoyl-5-([D₃]methyl)-2'-deoxycytidine

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