Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-benzenesulfonylmethyl-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-benzenesulfonylmethyl-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester
• CAS No.: 156430-65-8
• Molecular Formula: C₂₀H₂₀N₄O₈S
• Molecular Weight: 476.467

Synonyms:Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-benzenesulfonylmethyl-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-benzenesulfonylmethyl-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-benzenesulfonylmethyl-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester

There total 2 articles about Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-benzenesulfonylmethyl-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 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: 73.0%

2',3'-di-O-acetyl-5'-deoxy-5'-(phenylsulfonyl)adenosine (156430-70-5) → Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-benzenesulfonylmethyl-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester (156430-65-8)

Guidance literature:

With tert.-butylnitrite; In ethyl acetate; for 16h; Ambient temperature;

DOI:10.1080/15257779408013249

Reference yield:

2',3'-Di-O-acetyl-5'-S-phenyl-5'-thioadenosine (149725-73-5) → Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-benzenesulfonylmethyl-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester (156430-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / MCPBA / CH₂Cl₂ / -20 deg C, 3 h, -20 deg C to room temperature, 1 h

2: 73 percent / tert-butyl nitrite / ethyl acetate / 16 h / Ambient temperature

With tert.-butylnitrite; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; ethyl acetate;

DOI:10.1080/15257779408013249

Reference yield: 70.0%

Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-benzenesulfonylmethyl-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester (156430-65-8) → 5'-deoxy-5'-(phenylsulfonyl)inosine

Guidance literature:

With ammonia; In methanol; at 0 ℃; for 2h;

DOI:10.1080/15257779408013249

upstream raw materials:

2',3'-di-O-acetyl-5'-deoxy-5'-(phenylsulfonyl)adenosine

2',3'-Di-O-acetyl-5'-S-phenyl-5'-thioadenosine

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