(Rp,Sp)-N⁴-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-(N,N-diisopropylamino)-(2,2,2-trifluoroethyl)phosphoramidites

Base Information

• Chemical Name: (Rp,Sp)-N⁴-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-(N,N-diisopropylamino)-(2,2,2-trifluoroethyl)phosphoramidites
• CAS No.: 161000-52-8
• Molecular Formula: C₄₅H₅₀F₃N₄O₈P
• Molecular Weight: 862.883

Synonyms:(Rp,Sp)-N⁴-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-(N,N-diisopropylamino)-(2,2,2-trifluoroethyl)phosphoramidites

Chemical Property of (Rp,Sp)-N⁴-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-(N,N-diisopropylamino)-(2,2,2-trifluoroethyl)phosphoramidites

Chemical Property:

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Technology Process of (Rp,Sp)-N⁴-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-(N,N-diisopropylamino)-(2,2,2-trifluoroethyl)phosphoramidites

There total 1 articles about (Rp,Sp)-N⁴-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-(N,N-diisopropylamino)-(2,2,2-trifluoroethyl)phosphoramidites 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%

4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine (67219-55-0) + chloro-N,N-diisopropylamino-(2,2,2-trifluoroethoxy)phosphine (161000-51-7) → (Rp,Sp)-N4-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-(N,N-diisopropylamino)-(2,2,2-trifluoroethyl)phosphoramidites (161000-52-8)

Guidance literature:

With diisopropylamine; In dichloromethane; for 0.333333h; Ambient temperature;

DOI:10.1139/v94-193

Reference yield:

(Rp,Sp)-N4-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-(N,N-diisopropylamino)-(2,2,2-trifluoroethyl)phosphoramidites (161000-52-8) → (Rp)-N4-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidylyl-3',5'-N6-benzoyl-3'-O-<(1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine (2,2,2-trifluoroethyl)phosphate

Guidance literature:

Multi-step reaction with 2 steps

1: tetrazole / acetonitrile / 4 h / Ambient temperature

2: iodine, 2,6-lutidine / tetrahydrofuran; H₂O / 0.17 h

With 2,6-dimethylpyridine; 1H-tetrazole; iodine; In tetrahydrofuran; water; acetonitrile;

DOI:10.1139/v94-193

Reference yield:

(Rp,Sp)-N4-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-(N,N-diisopropylamino)-(2,2,2-trifluoroethyl)phosphoramidites (161000-52-8) → (Sp)-N4-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidylyl-3',5'-N6-benzoyl-3'-O-<(1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine (2,2,2-trifluoroethyl)phosphate

Guidance literature:

Multi-step reaction with 2 steps

1: tetrazole / acetonitrile / 4 h / Ambient temperature

2: iodine, 2,6-lutidine / tetrahydrofuran; H₂O / 0.17 h

With 2,6-dimethylpyridine; 1H-tetrazole; iodine; In tetrahydrofuran; water; acetonitrile;

DOI:10.1139/v94-193

upstream raw materials:

4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine

chloro-N,N-diisopropylamino-(2,2,2-trifluoroethoxy)phosphine

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