N⁴-acetyl-2'-C-cyano-2',3'-didehydro-2',3'-dideoxy-5'-O-(dimethoxytrityl)cytidine

Base Information

• Chemical Name: N⁴-acetyl-2'-C-cyano-2',3'-didehydro-2',3'-dideoxy-5'-O-(dimethoxytrityl)cytidine
• CAS No.: 140859-07-0
• Molecular Formula: C₃₃H₃₀N₄O₆
• Molecular Weight: 578.624

Synonyms:N⁴-acetyl-2'-C-cyano-2',3'-didehydro-2',3'-dideoxy-5'-O-(dimethoxytrityl)cytidine

Chemical Property of N⁴-acetyl-2'-C-cyano-2',3'-didehydro-2',3'-dideoxy-5'-O-(dimethoxytrityl)cytidine

Chemical Property:

Purity/Quality:

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Technology Process of N⁴-acetyl-2'-C-cyano-2',3'-didehydro-2',3'-dideoxy-5'-O-(dimethoxytrityl)cytidine

There total 7 articles about N⁴-acetyl-2'-C-cyano-2',3'-didehydro-2',3'-dideoxy-5'-O-(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: 90.0%

N4-acetyl-1-<2-C-cyano-2-deoxy-5-O-(dimethoxytrityl)-β-D-arabinofuranosyl>cytosine (140859-05-8) → N4-acetyl-2'-C-cyano-2',3'-didehydro-2',3'-dideoxy-5'-O-(dimethoxytrityl)cytidine (140859-07-0)

Guidance literature:

With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; for 3h; Ambient temperature;

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → N4-acetyl-2'-C-cyano-2',3'-didehydro-2',3'-dideoxy-5'-O-(dimethoxytrityl)cytidine (140859-07-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / pyridine / 1.5 h / Ambient temperature

2: 90 percent / N,N'-carbonyldiimidazole / dimethylformamide / 3 h / Ambient temperature

With pyridine; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide;

Reference yield:

N4-acetyl-1-<3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-erythro-pentofuran-2-ulosyl>cytosine (140859-16-1) → N4-acetyl-2'-C-cyano-2',3'-didehydro-2',3'-dideoxy-5'-O-(dimethoxytrityl)cytidine (140859-07-0)

Guidance literature:

Multi-step reaction with 6 steps

1: phosphate buffer / diethyl ether; tetrahydrofuran / 2 h / Ambient temperature

2: DMAP, Et₃N / acetonitrile / 2 h / Ambient temperature

3: Bu₃SnH, AIBN / toluene / 3 h / 100 °C

4: 84 percent / AcOH, TBAF / tetrahydrofuran / 0.25 h / Ambient temperature

5: 83 percent / pyridine / 1.5 h / Ambient temperature

6: 90 percent / N,N'-carbonyldiimidazole / dimethylformamide / 3 h / Ambient temperature

With pyridine; dmap; phosphate buffer; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; acetic acid; triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

N⁴-acetyl-1-<2-C-cyano-2-deoxy-5-O-(dimethoxytrityl)-β-D-arabinofuranosyl>cytosine

4,4'-dimethoxytrityl chloride

N⁴-acetyl-1-(2-C-cyano-2-deoxy-β-D-arabinofuranosyl)cytosine

N⁴-acetyl-1-<2-C-cyano-2-deoxy-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl>cytosine

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