N⁴-benzoyl-1-{(S)-2-[(diisopropoxyphosphoryl)methoxy]-3-(triphenylmethoxy)propyl}-5-[(trimethylsilyl)ethynyl]cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-{(S)-2-[(diisopropoxyphosphoryl)methoxy]-3-(triphenylmethoxy)propyl}-5-[(trimethylsilyl)ethynyl]cytosine
• CAS No.: 897931-73-6
• Molecular Formula: C₄₅H₅₂N₃O₇PSi
• Molecular Weight: 805.983

Synonyms:N⁴-benzoyl-1-{(S)-2-[(diisopropoxyphosphoryl)methoxy]-3-(triphenylmethoxy)propyl}-5-[(trimethylsilyl)ethynyl]cytosine

Chemical Property of N⁴-benzoyl-1-{(S)-2-[(diisopropoxyphosphoryl)methoxy]-3-(triphenylmethoxy)propyl}-5-[(trimethylsilyl)ethynyl]cytosine

Chemical Property:

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Technology Process of N⁴-benzoyl-1-{(S)-2-[(diisopropoxyphosphoryl)methoxy]-3-(triphenylmethoxy)propyl}-5-[(trimethylsilyl)ethynyl]cytosine

There total 2 articles about N⁴-benzoyl-1-{(S)-2-[(diisopropoxyphosphoryl)methoxy]-3-(triphenylmethoxy)propyl}-5-[(trimethylsilyl)ethynyl]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: 70.0%

N4-benzoyl-1-{(S)-2-[(diisopropoxyphosphoryl)methoxy]-3-(triphenylmethoxy)propyl}-5-iodocytosine (897931-72-5) + trimethylsilylacetylene (1066-54-2) → N4-benzoyl-1-{(S)-2-[(diisopropoxyphosphoryl)methoxy]-3-(triphenylmethoxy)propyl}-5-[(trimethylsilyl)ethynyl]cytosine (897931-73-6)

Guidance literature:

With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 20 ℃; for 2h;

DOI:10.1135/cccc20060579

Reference yield:

bis(2-propyl) N4-benzoyl-1-(S)-(2-phosphonomethoxy-3-triphenylmethoxypropyl)cytosine (148873-52-3) → N4-benzoyl-1-{(S)-2-[(diisopropoxyphosphoryl)methoxy]-3-(triphenylmethoxy)propyl}-5-[(trimethylsilyl)ethynyl]cytosine (897931-73-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / N-iodosuccinimide; AIBN / toluene / 16 h / 20 - 80 °C

2: 70 percent / CuI; Et₃N / [PdCl₂(Ph₃P)2] / dioxane / 2 h / 20 °C

With N-iodo-succinimide; copper(l) iodide; 2,2'-azobis(isobutyronitrile); triethylamine; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; toluene; 2: Sonogashira coupling;

DOI:10.1135/cccc20060579

Reference yield: 96.0%

N4-benzoyl-1-{(S)-2-[(diisopropoxyphosphoryl)methoxy]-3-(triphenylmethoxy)propyl}-5-[(trimethylsilyl)ethynyl]cytosine (897931-73-6) → 1-{(S)-2-[(diisopropoxyphosphoryl)methoxy]-3-(triphenylmethoxy)propyl}-5-ethynylcytosine (897931-74-7)

Guidance literature:

With ammonia; In methanol; at 4 ℃; for 24h;

DOI:10.1135/cccc20060579

upstream raw materials:

N⁴-benzoyl-1-{(S)-2-[(diisopropoxyphosphoryl)methoxy]-3-(triphenylmethoxy)propyl}-5-iodocytosine

trimethylsilylacetylene

bis(2-propyl) N⁴-benzoyl-1-(S)-(2-phosphonomethoxy-3-triphenylmethoxypropyl)cytosine

Downstream raw materials:

1-{(S)-2-[(diisopropoxyphosphoryl)methoxy]-3-(triphenylmethoxy)propyl}-5-ethynylcytosine

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