N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine

Base Information

• Chemical Name: N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine
• CAS No.: 911110-85-5
• Molecular Formula: C₃₇H₃₇F₃N₆O₈
• Molecular Weight: 750.731

Synonyms:N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine

Chemical Property of N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine

Chemical Property:

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Technology Process of N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine

There total 5 articles about N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]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: 74.0%

N2-acetyl-9-[2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine (911110-84-4) + 4,4'-dimethoxytrityl chloride (40615-36-9) → N2-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine (911110-85-5)

Guidance literature:

With pyridine; at 20 ℃; for 5.5h;

DOI:10.1002/ejoc.200600182

Reference yield:

N2-acetyl-6-chloro-9-[3',5'-di-O-acetyl-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine (911110-82-2) → N2-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine (911110-85-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 58 percent / Et₃N; H₂ / Pd/C / methanol / 5 h

2: 86 percent / Na₂CO₃ / methanol / 1 h / 20 °C

3: 74 percent / pyridine; MS / 5.5 h / 20 °C

With pyridine; hydrogen; sodium carbonate; triethylamine; palladium on activated charcoal; In methanol;

DOI:10.1002/ejoc.200600182

Reference yield:

N-(6-chloro-7(9)H-purin-2-yl)-acetamide (7602-01-9) → N2-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine (911110-85-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: BSA / 1,2-dichloro-ethane / 0.5 h / 80 °C

1.2: 68 percent / TMSOTf / toluene / 2.5 h / 80 °C

2.1: 58 percent / Et₃N; H₂ / Pd/C / methanol / 5 h

3.1: 86 percent / Na₂CO₃ / methanol / 1 h / 20 °C

4.1: 74 percent / pyridine; MS / 5.5 h / 20 °C

With pyridine; benzenesulfonamide; hydrogen; sodium carbonate; triethylamine; palladium on activated charcoal; In methanol; 1,2-dichloro-ethane; 1.2: Vorbrueggen reaction;

DOI:10.1002/ejoc.200600182

upstream raw materials:

N²-acetyl-9-[2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine

4,4'-dimethoxytrityl chloride

N²-acetyl-9-[3',5'-di-O-acetyl-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine

N²-acetyl-6-chloro-9-[3',5'-di-O-acetyl-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine

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