9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2-acetamidopurine-6-thiol

Base Information

• Chemical Name: 9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2-acetamidopurine-6-thiol
• CAS No.: 109303-96-0
• Molecular Formula: C₂₁H₂₀FN₅O₆S
• Molecular Weight: 489.484

Synonyms:9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2-acetamidopurine-6-thiol

Chemical Property of 9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2-acetamidopurine-6-thiol

Chemical Property:

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Technology Process of 9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2-acetamidopurine-6-thiol

There total 3 articles about 9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2-acetamidopurine-6-thiol 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: 82.0%

9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2-acetamido-6-chloropurine (109303-94-8) → 9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2-acetamidopurine-6-thiol (109303-96-0)

Guidance literature:

With thiourea; In propan-1-ol; for 2h; Heating;

DOI:10.1248/cpb.37.336

Reference yield:

1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (56632-81-6) → 9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2-acetamidopurine-6-thiol (109303-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Me₃SiCl, Et₃N; 2.) Hg(CN)2 / 1.) PhH, 40 h; 2.) PhH, reflux. 4 h

2: 82 percent / thiourea / propan-1-ol / 2 h / Heating

With chloro-trimethyl-silane; mercury(II) cyanide; triethylamine; thiourea; In propan-1-ol;

DOI:10.1248/cpb.37.336

Reference yield:

N-(6-chloro-7(9)H-purin-2-yl)-acetamide (7602-01-9) → 9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2-acetamidopurine-6-thiol (109303-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Me₃SiCl, Et₃N; 2.) Hg(CN)2 / 1.) PhH, 40 h; 2.) PhH, reflux. 4 h

2: 82 percent / thiourea / propan-1-ol / 2 h / Heating

With chloro-trimethyl-silane; mercury(II) cyanide; triethylamine; thiourea; In propan-1-ol;

DOI:10.1248/cpb.37.336

upstream raw materials:

9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2-acetamido-6-chloropurine

1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide

N-(6-chloro-7⁽⁹⁾H-purin-2-yl)-acetamide

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