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

Base Information

• Chemical Name: N⁴-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl
• CAS No.: 600723-93-1
• Molecular Formula: C₄₅H₅₅N₇O₁₀P₂
• Molecular Weight: 915.92

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

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

Chemical Property:

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

There total 3 articles about N⁴-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl 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: 50.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + N4-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine (600723-92-0) → N4-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidin-3'-yl (600723-93-1)

Guidance literature:

With N,N-diisopropyl-1,2-ethanediamine; In dichloromethane; at 20 ℃; for 0.5h;

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)cytidin-3'-yl (600723-93-1)

Guidance literature:

Multi-step reaction with 2 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

With 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)cytidin-3'-yl (600723-93-1)

Guidance literature:

Multi-step reaction with 2 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

With 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:

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

N⁴-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine

bis(2-cyanoethyl) diisopropylamidophosphite

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

Downstream raw materials:

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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