5-[2-(5-butylpyrid-2-yl)ethynyl]-1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]uracil

Base Information

Chemical Name:5-[2-(5-butylpyrid-2-yl)ethynyl]-1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]uracil
CAS No.:948559-95-3
Molecular Formula:C₃₆H₃₅N₃O₇
Molecular Weight:621.69
Hs Code.:

Synonyms:5-[2-(5-butylpyrid-2-yl)ethynyl]-1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]uracil

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Chemical Property of 5-[2-(5-butylpyrid-2-yl)ethynyl]-1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]uracil

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Technology Process of 5-[2-(5-butylpyrid-2-yl)ethynyl]-1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]uracil

There total 4 articles about 5-[2-(5-butylpyrid-2-yl)ethynyl]-1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]uracil 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: 97.0%

: 136723-73-4
C₁₁H₁₃N

: 31356-86-2
1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodouracil

: 948559-95-3
5-[2-(5-butylpyrid-2-yl)ethynyl]-1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]uracil

Guidance literature:: With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; at 50 ℃; for 1.5h;
DOI:10.1021/jm070210n

Reference yield:

: 626-55-1,163928-56-1
3-Bromopyridine

: 948559-95-3
5-[2-(5-butylpyrid-2-yl)ethynyl]-1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]uracil

Guidance literature:: Multi-step reaction with 4 steps

1.1: CuBr / tetrahydrofuran

2.1: BuLi; LiDMAE / hexane / 0 °C

2.2: CBr₄ / tetrahydrofuran

3.1: triethylamine / (Ph₃P)4Pd; CuI / CH₂Cl₂ / 2 h / 50 °C

3.2: 57 percent / TBAF / tetrahydrofuran / 0.5 h

4.1: 97 percent / triethylamine / (Ph₃P)4Pd; CuI / CH₂Cl₂ / 1.5 h / 50 °C

With n-butyllithium; triethylamine; copper(I) bromide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; 3.1: Sonogashira coupling / 4.1: Sonogashira coupling;
DOI:10.1021/jm070210n

Reference yield:

: 539-32-2
3-butylpyridine

: 948559-95-3
5-[2-(5-butylpyrid-2-yl)ethynyl]-1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]uracil

Guidance literature:: Multi-step reaction with 3 steps

1.1: BuLi; LiDMAE / hexane / 0 °C

1.2: CBr₄ / tetrahydrofuran

2.1: triethylamine / (Ph₃P)4Pd; CuI / CH₂Cl₂ / 2 h / 50 °C

2.2: 57 percent / TBAF / tetrahydrofuran / 0.5 h

3.1: 97 percent / triethylamine / (Ph₃P)4Pd; CuI / CH₂Cl₂ / 1.5 h / 50 °C

With n-butyllithium; triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In hexane; dichloromethane; 2.1: Sonogashira coupling / 3.1: Sonogashira coupling;
DOI:10.1021/jm070210n