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

Base Information

• Chemical Name: N⁴-acetyl-1-<2-C-cyano-2-deoxy-5-O-(dimethoxytrityl)-β-D-arabinofuranosyl>cytosine
• CAS No.: 140859-05-8
• Molecular Formula: C₃₃H₃₂N₄O₇
• Molecular Weight: 596.64
• Mol file: 140859-05-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about N⁴-acetyl-1-<2-C-cyano-2-deoxy-5-O-(dimethoxytrityl)-β-D-arabinofuranosyl>cytosine 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: 83.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + N4-acetyl-1-(2-C-cyano-2-deoxy-β-D-arabinofuranosyl)cytosine (135598-72-0) → N4-acetyl-1-<2-C-cyano-2-deoxy-5-O-(dimethoxytrityl)-β-D-arabinofuranosyl>cytosine (140859-05-8)

Guidance literature:

With pyridine; for 1.5h; Ambient temperature;

Reference yield:

N4-acetyl-1-<3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-erythro-pentofuran-2-ulosyl>cytosine (140859-16-1) → N4-acetyl-1-<2-C-cyano-2-deoxy-5-O-(dimethoxytrityl)-β-D-arabinofuranosyl>cytosine (140859-05-8)

Guidance literature:

Multi-step reaction with 5 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

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

Reference yield:

N-[1-((2R,3aR,9aR)-3-Cyano-3-hydroxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acetamide → N4-acetyl-1-<2-C-cyano-2-deoxy-5-O-(dimethoxytrityl)-β-D-arabinofuranosyl>cytosine (140859-05-8)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 84 percent / AcOH, TBAF / tetrahydrofuran / 0.25 h / Ambient temperature

4: 83 percent / pyridine / 1.5 h / Ambient temperature

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; acetic acid; triethylamine; In tetrahydrofuran; toluene; acetonitrile;

upstream raw materials:

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

N⁴-acetyl-1-<3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-erythro-pentofuran-2-ulosyl>cytosine

Downstream raw materials:

C₆₇H₆₇N₆O₁₆P

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