(1R,3R,4R,7S)-3-[5-(3-cholesterylcarbonylaminopropyn-1-yl)uracil-1-yl]-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1R,3R,4R,7S)-3-[5-(3-cholesterylcarbonylaminopropyn-1-yl)uracil-1-yl]-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane
• CAS No.: 1252654-41-3
• Molecular Formula: C₆₂H₇₇N₃O₁₀
• Molecular Weight: 1024.31
• Mol file: 1252654-41-3.mol

Synonyms:(1R,3R,4R,7S)-3-[5-(3-cholesterylcarbonylaminopropyn-1-yl)uracil-1-yl]-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane

Chemical Property of (1R,3R,4R,7S)-3-[5-(3-cholesterylcarbonylaminopropyn-1-yl)uracil-1-yl]-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4R,7S)-3-[5-(3-cholesterylcarbonylaminopropyn-1-yl)uracil-1-yl]-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane

There total 3 articles about (1R,3R,4R,7S)-3-[5-(3-cholesterylcarbonylaminopropyn-1-yl)uracil-1-yl]-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane 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: 53.0%

(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(5-iodoracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (1202937-23-2) + cholesterylprop-2-ynylcarbamate amine (942400-20-6) → (1R,3R,4R,7S)-3-[5-(3-cholesterylcarbonylaminopropyn-1-yl)uracil-1-yl]-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane (1252654-41-3)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 12h; Inert atmosphere; Darkness;

DOI:10.1021/jo500614a

Reference yield:

1-((1S,3R,4R,7S)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)pyrimidine-2,4(1H,3H)-dione (200435-92-3) → (1R,3R,4R,7S)-3-[5-(3-cholesterylcarbonylaminopropyn-1-yl)uracil-1-yl]-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane (1252654-41-3)

Guidance literature:

Multi-step reaction with 3 steps

1: iodine; ammonium cerium (IV) nitrate / acetic acid / 0.67 h / 80 °C / Inert atmosphere

2: pyridine / 16 h / 20 °C / Inert atmosphere

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

With pyridine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium cerium (IV) nitrate; iodine; triethylamine; In acetic acid; N,N-dimethyl-formamide; 3: |Sonogashira Cross-Coupling;

DOI:10.1021/jo500614a

Reference yield:

(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(5-iodoracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (1202937-22-1) → (1R,3R,4R,7S)-3-[5-(3-cholesterylcarbonylaminopropyn-1-yl)uracil-1-yl]-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane (1252654-41-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 16 h / 20 °C / Inert atmosphere

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

With pyridine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In N,N-dimethyl-formamide; 2: |Sonogashira Cross-Coupling;

DOI:10.1021/jo500614a

upstream raw materials:

(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(5-iodoracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

cholesterylprop-2-ynylcarbamate amine

1-((1S,3R,4R,7S)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)pyrimidine-2,4(1H,3H)-dione

(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(5-iodoracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Downstream raw materials:

(1R,3R,4R,7S)-3-[5-(3-cholesterylcarbonylaminopropyn-1-yl)-uracil-1-yl]-7-[2-cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-2,5-dioxabicyclo[2.2.1]heptane