N⁴-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)cytidylyl-(3'->5')-3'-O-acetylthymidine

Base Information

• Chemical Name: N⁴-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)cytidylyl-(3'->5')-3'-O-acetylthymidine
• CAS No.: 600723-94-2
• Molecular Formula: C₅₁H₅₆N₈O₁₇P₂
• Molecular Weight: 1115

Synonyms:N⁴-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)cytidylyl-(3'->5')-3'-O-acetylthymidine

Chemical Property of N⁴-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)cytidylyl-(3'->5')-3'-O-acetylthymidine

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Technology Process of N⁴-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)cytidylyl-(3'->5')-3'-O-acetylthymidine

There total 4 articles about N⁴-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)cytidylyl-(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: 93.0%

3'-O-acetylthymidine (21090-30-2) + N4-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl (600723-93-1) → N4-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)cytidylyl-(3'->5')-3'-O-acetylthymidine (600723-94-2)

Guidance literature:

3'-O-acetylthymidine; N⁴-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl; 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:

bis(2-cyanoethyl) diisopropylamidophosphite (102690-88-0) → N4-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)cytidylyl-(3'->5')-3'-O-acetylthymidine (600723-94-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hexamethyldisilazane / acetonitrile / 1 h / 20 °C

1.2: 1H-tetrazole / acetonitrile / 1 h / 20 °C

1.3: 32 percent / tert-butyl hydroperoxide / 0.25 h / 20 °C

2.1: 50 percent / N,N-diisopropylethyleneamine / CH₂Cl₂ / 0.5 h / 20 °C

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

3.2: 93 percent / tert-butyl hydroperoxide / acetonitrile / 0.25 h / 20 °C

With 1H-tetrazole; N,N-diisopropyl-1,2-ethanediamine; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; acetonitrile;

DOI:10.1002/ejoc.200200294

Reference yield:

5'-O-(4,4'-dimethoxytrityl)deoxycytidine (76512-82-8) → N4-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-P-(2-cyanoethyl)cytidylyl-(3'->5')-3'-O-acetylthymidine (600723-94-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hexamethyldisilazane / acetonitrile / 1 h / 20 °C

1.2: 1H-tetrazole / acetonitrile / 1 h / 20 °C

1.3: 32 percent / tert-butyl hydroperoxide / 0.25 h / 20 °C

2.1: 50 percent / N,N-diisopropylethyleneamine / CH₂Cl₂ / 0.5 h / 20 °C

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

3.2: 93 percent / tert-butyl hydroperoxide / acetonitrile / 0.25 h / 20 °C

With 1H-tetrazole; N,N-diisopropyl-1,2-ethanediamine; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; acetonitrile;

DOI:10.1002/ejoc.200200294

upstream raw materials:

3'-O-acetylthymidine

N⁴-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl

bis(2-cyanoethyl) diisopropylamidophosphite

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

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