2'-deoxy-N⁴-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl 2-cyanoethyl-N,N-diisopropylphosphoramidite

Base Information

• Chemical Name: 2'-deoxy-N⁴-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl 2-cyanoethyl-N,N-diisopropylphosphoramidite
• CAS No.: 600723-97-5
• Molecular Formula: C₄₃H₅₇N₅O₁₀P₂
• Molecular Weight: 865.901

Synonyms:2'-deoxy-N⁴-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl 2-cyanoethyl-N,N-diisopropylphosphoramidite

Chemical Property of 2'-deoxy-N⁴-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl 2-cyanoethyl-N,N-diisopropylphosphoramidite

Chemical Property:

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Technology Process of 2'-deoxy-N⁴-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl 2-cyanoethyl-N,N-diisopropylphosphoramidite

There total 2 articles about 2'-deoxy-N⁴-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl 2-cyanoethyl-N,N-diisopropylphosphoramidite 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: 51.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + 2'-deoxy-N4-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)cytidine (600723-96-4) → 2'-deoxy-N4-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl 2-cyanoethyl-N,N-diisopropylphosphoramidite (600723-97-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/ejoc.200200294

Reference yield:

5'-O-(4,4'-dimethoxytrityl)deoxycytidine (76512-82-8) → 2'-deoxy-N4-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl 2-cyanoethyl-N,N-diisopropylphosphoramidite (600723-97-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ClSiMe₃; triethylamine / CH₂Cl₂ / 0.5 h / 20 °C

1.2: CH₂Cl₂ / 0.5 h / 20 °C

1.3: 74 percent / tert-butyl hydroperoxide / CH₂Cl₂ / 0.25 h / 20 °C

2.1: 51 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 1 h / 20 °C

With chloro-trimethyl-silane; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1002/ejoc.200200294

Reference yield: 84.0%

3'-O-acetylthymidine (21090-30-2) + 2'-deoxy-N4-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl 2-cyanoethyl-N,N-diisopropylphosphoramidite (600723-97-5) → 2'-deoxy-N4-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)cytidyl-(3'->5')-3'-O-acetylthymidine (600723-98-6)

Guidance literature:

3'-O-acetylthymidine; 2'-deoxy-N⁴-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl 2-cyanoethyl-N,N-diisopropylphosphoramidite; With 1H-tetrazole; In acetonitrile; at 20 ℃; for 0.5h;

With tert.-butylhydroperoxide; In acetonitrile; at 20 ℃; for 0.25h;

DOI:10.1002/ejoc.200200294

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

2'-deoxy-N⁴-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)cytidine

5'-O-(4,4'-dimethoxytrityl)deoxycytidine

Downstream raw materials:

2'-deoxy-N⁴-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)cytidyl-(3'->5')-3'-O-acetylthymidine

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