(1S,3R,4S,7R)-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:(1S,3R,4S,7R)-3-[5-(3-cholesterylcarbonylaminopropyn-1-yl)uracil-1-yl]-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane
CAS No.:1275611-20-5
Molecular Formula:C₆₂H₇₇N₃O₁₀
Molecular Weight:1024.31
Hs Code.:

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

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

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

There total 12 articles about (1S,3R,4S,7R)-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: 76.0%

: 1275611-14-7
(1S,3R,4S,7R)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-3-(5-iodoracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

: 942400-20-6
cholesterylprop-2-ynylcarbamate amine

: 1275611-20-5
(1S,3R,4S,7R)-3-[5-(3-cholesterylcarbonylaminopropyn-1-yl)uracil-1-yl]-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane

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/jo5006153

Reference yield:

: 410076-93-6
3-O-benzyl-1,2-di-O-acetyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α,β-L-threo-pentofuranose

: 1275611-20-5
(1S,3R,4S,7R)-3-[5-(3-cholesterylcarbonylaminopropyn-1-yl)uracil-1-yl]-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 12 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / Inert atmosphere; Reflux

1.2: 28 h / Inert atmosphere; Reflux

2.1: hydrogenchloride / methanol / 24 h / 20 °C

3.1: pyridine / 4 h / 20 °C / Inert atmosphere

4.1: sodium hydroxide / 1,4-dioxane; water / 4 h / 20 °C

5.1: N,N-dimethyl-formamide / 20 h / 90 °C / Inert atmosphere

6.1: ammonia / methanol / 14 h / 20 °C

7.1: palladium on carbon / methanol; tetrahydrofuran; formic acid / 24 h / Reflux

8.1: pyridine / 14 h / 60 °C / Inert atmosphere

9.1: iodine; ammonium cerium (IV) nitrate / acetic acid / 0.83 h / 80 °C

10.1: ammonia / methanol / 12 h / 20 °C

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

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

With pyridine; hydrogenchloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N,O-bis-(trimethylsilyl)-acetamide; ammonium cerium (IV) nitrate; palladium on carbon; ammonia; iodine; triethylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; formic acid; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1.1: |Vorbrueggen Nucleoside Synthesis / 12.1: |Sonogashira Cross-Coupling;
DOI:10.1021/jo5006153

Reference yield:

: 1275611-13-6
C₁₀H₁₁IN₂O₆

: 1275611-20-5
(1S,3R,4S,7R)-3-[5-(3-cholesterylcarbonylaminopropyn-1-yl)uracil-1-yl]-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane

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/jo5006153