3',5'-di-O-acetyl-N-[4-(2,6-dihydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine

Base Information

Chemical Name:3',5'-di-O-acetyl-N-[4-(2,6-dihydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine
CAS No.:1332507-64-8
Molecular Formula:C₂₄H₂₈BrN₃O₁₀
Molecular Weight:598.404
Hs Code.:

Synonyms:3',5'-di-O-acetyl-N-[4-(2,6-dihydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine

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Chemical Property of 3',5'-di-O-acetyl-N-[4-(2,6-dihydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine

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Technology Process of 3',5'-di-O-acetyl-N-[4-(2,6-dihydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine

There total 5 articles about 3',5'-di-O-acetyl-N-[4-(2,6-dihydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine 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:

: 1332507-68-2
4-O-pivaloyl-2-aminophloroglucinol

: ((2R,3S,5R)-3-acetoxy-5-(5-bromo-4-chloro-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate

: 1332507-64-8
3',5'-di-O-acetyl-N-[4-(2,6-dihydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine

Guidance literature:: 4-O-pivaloyl-2-aminophloroglucinol; ((2R,3S,5R)-3-acetoxy-5-(5-bromo-4-chloro-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;

In tetrachloromethane;
DOI:10.1016/j.tet.2011.03.111

Reference yield:

: C₁₁H₁₃NO₆

: 1332507-64-8
3',5'-di-O-acetyl-N-[4-(2,6-dihydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine

Guidance literature:: Multi-step reaction with 2 steps

1: 5%-palladium/activated carbon; hydrogen / methanol / 2.5 h / 0 - 20 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 12 h / 20 °C / Inert atmosphere

With 5%-palladium/activated carbon; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane;
DOI:10.1016/j.tet.2011.03.111

Reference yield:

: 108-73-6
3,5-dihydroxyphenol

: 1332507-64-8
3',5'-di-O-acetyl-N-[4-(2,6-dihydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine

Guidance literature:: Multi-step reaction with 4 steps

1: sulfuric acid; nitric acid / 3 h / 20 °C

2: pyridine / 2 h / 0 - 20 °C / Inert atmosphere

3: 5%-palladium/activated carbon; hydrogen / methanol / 2.5 h / 0 - 20 °C

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 12 h / 20 °C / Inert atmosphere

With pyridine; sulfuric acid; 5%-palladium/activated carbon; hydrogen; nitric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane;
DOI:10.1016/j.tet.2011.03.111