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

Base Information

• Chemical Name: 2'-deoxy-N⁴-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)cytidyl-(3'->5')-3'-O-acetylthymidine
• CAS No.: 600723-98-6
• Molecular Formula: C₄₉H₅₈N₆O₁₇P₂
• Molecular Weight: 1064.98

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

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

Chemical Property:

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

There total 3 articles about 2'-deoxy-N⁴-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)cytidyl-(3'->5')-3'-O-acetylthymidine 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: 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

Reference yield:

5'-O-(4,4'-dimethoxytrityl)deoxycytidine (76512-82-8) → 2'-deoxy-N4-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)cytidyl-(3'->5')-3'-O-acetylthymidine (600723-98-6)

Guidance literature:

Multi-step reaction with 3 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

3.1: 1H-tetrazole / acetonitrile / 0.5 h / 20 °C

3.2: 84 percent / tert-butyl hydroperoxide / acetonitrile / 0.25 h / 20 °C

With 1H-tetrazole; chloro-trimethyl-silane; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;

DOI:10.1002/ejoc.200200294

Reference yield:

2'-deoxy-N4-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)cytidine (600723-96-4) → 2'-deoxy-N4-diethoxyphosphoryl-5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)cytidyl-(3'->5')-3'-O-acetylthymidine (600723-98-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 51 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 1 h / 20 °C

2.1: 1H-tetrazole / acetonitrile / 0.5 h / 20 °C

2.2: 84 percent / tert-butyl hydroperoxide / acetonitrile / 0.25 h / 20 °C

With 1H-tetrazole; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;

DOI:10.1002/ejoc.200200294

upstream raw materials:

3'-O-acetylthymidine

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

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

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

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