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

Base Information

• Chemical Name: N⁴-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine
• CAS No.: 600723-92-0
• Molecular Formula: C₃₆H₃₈N₅O₉P
• Molecular Weight: 715.7
• Mol file: 600723-92-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about N⁴-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine 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: 32.0%

bis(2-cyanoethyl) diisopropylamidophosphite (102690-88-0) + 5'-O-(4,4'-dimethoxytrityl)deoxycytidine (76512-82-8) → N4-bis(2-cyanoethoxy)phosphoryl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine (600723-92-0)

Guidance literature:

5'-O-(4,4'-dimethoxytrityl)deoxycytidine; With 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile; at 20 ℃; for 1h;

bis(2-cyanoethyl) diisopropylamidophosphite; With 1H-tetrazole; In acetonitrile; at 20 ℃; for 1h;

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

DOI:10.1002/ejoc.200200294

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:

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)-P-(2-cyanoethyl)cytidylyl-(3'->5')-3'-O-acetylthymidine (600723-94-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 50 percent / N,N-diisopropylethyleneamine / CH₂Cl₂ / 0.5 h / 20 °C

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

2.2: 93 percent / tert-butyl hydroperoxide / acetonitrile / 0.25 h / 20 °C

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

DOI:10.1002/ejoc.200200294

upstream raw materials:

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)cytidin-3'-yl

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