6-methyl-9-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}purine

Base Information

• Chemical Name: 6-methyl-9-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}purine
• CAS No.: 1312944-80-1
• Molecular Formula: C₂₆H₂₄FN₅O₆
• Molecular Weight: 521.505

Synonyms:6-methyl-9-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}purine

Chemical Property of 6-methyl-9-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}purine

Chemical Property:

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Technology Process of 6-methyl-9-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}purine

There total 10 articles about 6-methyl-9-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}purine 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: 69.0%

6-methyl-9-{(5E)-5,6,7-trideoxy-7-[6-(4-fluorophenyl)-2,2-bis(4-methoxyphenyl)-1,3-benzodioxole-4-carboxamido]-β-D-ribo-hept-5-enofuranosyl}-purine (1312944-68-5) → 6-methyl-9-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}purine (1312944-80-1)

Guidance literature:

With trifluoroacetic acid; In water; at 0 ℃; for 0.666667h; Inert atmosphere;

DOI:10.1002/chem.201003648

Reference yield:

6-bromo-2,2-bis-(4-methoxy-phenyl)-benzo[1,3]dioxole-4-carboxylic acid methyl ester → 6-methyl-9-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}purine (1312944-80-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; water; toluene / 3 h / 100 °C / Inert atmosphere

2.1: lithium hydroxide monohydrate / 70 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

3.2: 5 h / 0 °C / Inert atmosphere

4.1: trifluoroacetic acid / water / 0.67 h / 0 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium hydroxide monohydrate; potassium carbonate; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In ethanol; water; N,N-dimethyl-formamide; toluene; 1.1: Suzuki coupling;

DOI:10.1002/chem.201003648

Reference yield:

2,3-Dihydroxybenzoic acid (303-38-8) → 6-methyl-9-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}purine (1312944-80-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: bromine; acetic acid / 20 h / 20 °C / Inert atmosphere

2.1: thionyl chloride / 15 h / 65 °C / Inert atmosphere

3.1: oxalyl dichloride / 3 h / 60 - 160 °C / Inert atmosphere

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; water; toluene / 3 h / 100 °C / Inert atmosphere

5.1: lithium hydroxide monohydrate / 70 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

6.2: 5 h / 0 °C / Inert atmosphere

7.1: trifluoroacetic acid / water / 0.67 h / 0 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; oxalyl dichloride; lithium hydroxide monohydrate; bromine; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In ethanol; water; N,N-dimethyl-formamide; toluene; 4.1: Suzuki coupling;

DOI:10.1002/chem.201003648

upstream raw materials:

(E)-1,2,3-tri-O-acetyl-5,6,7-trideoxy-7-C-phthalimido-D-ribohept-5-enofuranose

methyl 6-(4-fluorophenyl)-2,2-bis(4-methoxyphenyl)-1,3-benzodioxole-4-carboxylate

6-(4-fluorophenyl)-2,2-bis(4-methoxyphenyl)-1,3-benzodioxole-4-carboxylic acid

6-methyl-9-{(5E)-5,6,7-trideoxy-7-[6-(4-fluorophenyl)-2,2-bis(4-methoxyphenyl)-1,3-benzodioxole-4-carboxamido]-β-D-ribo-hept-5-enofuranosyl}-purine

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