N⁴-acetyl-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-{3-[di(prop-2-ynyl)amino]prop-1-ynyl}-cytosine 3'-(2-cyanoethyl)-N,N'-diisopropyl phosphoramidite

Base Information

• Chemical Name: N⁴-acetyl-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-{3-[di(prop-2-ynyl)amino]prop-1-ynyl}-cytosine 3'-(2-cyanoethyl)-N,N'-diisopropyl phosphoramidite
• CAS No.: 1431298-68-8
• Molecular Formula: C₅₀H₅₇N₆O₈P
• Molecular Weight: 901.012

Synonyms:N⁴-acetyl-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-{3-[di(prop-2-ynyl)amino]prop-1-ynyl}-cytosine 3'-(2-cyanoethyl)-N,N'-diisopropyl phosphoramidite

Chemical Property of N⁴-acetyl-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-{3-[di(prop-2-ynyl)amino]prop-1-ynyl}-cytosine 3'-(2-cyanoethyl)-N,N'-diisopropyl phosphoramidite

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Technology Process of N⁴-acetyl-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-{3-[di(prop-2-ynyl)amino]prop-1-ynyl}-cytosine 3'-(2-cyanoethyl)-N,N'-diisopropyl phosphoramidite

There total 4 articles about N⁴-acetyl-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-{3-[di(prop-2-ynyl)amino]prop-1-ynyl}-cytosine 3'-(2-cyanoethyl)-N,N'-diisopropyl phosphoramidite 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: 67.0%

N4-acetyl-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-{3-[di(prop-2-ynyl)amino]prop-1-ynyl}cytosine (1431298-67-7) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → N4-acetyl-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-{3-[di(prop-2-ynyl)amino]prop-1-ynyl}-cytosine 3'-(2-cyanoethyl)-N,N'-diisopropyl phosphoramidite (1431298-68-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tet.2013.03.054

Reference yield:

tripopargylamine (6921-29-5) → N4-acetyl-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-{3-[di(prop-2-ynyl)amino]prop-1-ynyl}-cytosine 3'-(2-cyanoethyl)-N,N'-diisopropyl phosphoramidite (1431298-68-8)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; copper(l) iodide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

2: pyridine / 8 h / 20 °C

3: N,N-dimethyl-formamide / 20 h / 20 °C

4: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With pyridine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; 1: |Sonogashira Cross-Coupling;

DOI:10.1016/j.tet.2013.03.054

Reference yield:

1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-{3-[di(prop-2-ynyl)amino]prop-1-ynyl}cytosine (1431298-65-5) → N4-acetyl-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-{3-[di(prop-2-ynyl)amino]prop-1-ynyl}-cytosine 3'-(2-cyanoethyl)-N,N'-diisopropyl phosphoramidite (1431298-68-8)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 8 h / 20 °C

2: N,N-dimethyl-formamide / 20 h / 20 °C

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With pyridine; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2013.03.054

upstream raw materials:

tripopargylamine

1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-{3-[di(prop-2-ynyl)amino]prop-1-ynyl}cytosine

N⁴-acetyl-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-{3-[di(prop-2-ynyl)amino]prop-1-ynyl}cytosine

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

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