((2R,3S,4R,5S)-3-acetoxy-5-(6-chloro-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate

Base Information

• Chemical Name: ((2R,3S,4R,5S)-3-acetoxy-5-(6-chloro-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate
• CAS No.: 1187434-00-9
• Molecular Formula: C₂₁H₂₀ClFN₄O₅
• Molecular Weight: 462.865

Synonyms:((2R,3S,4R,5S)-3-acetoxy-5-(6-chloro-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate

Chemical Property of ((2R,3S,4R,5S)-3-acetoxy-5-(6-chloro-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate

Chemical Property:

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Technology Process of ((2R,3S,4R,5S)-3-acetoxy-5-(6-chloro-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate

There total 2 articles about ((2R,3S,4R,5S)-3-acetoxy-5-(6-chloro-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate 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:

(3R,4S,5R)-5-(benzoyloxymethyl)-3-fluoro-3,4-dimethyltetrahydrofuran-2,4-diyl diacetate (1187433-95-9) + 6-chloro-7H-purine (87-42-3,111055-92-6) → ((2R,3S,4R,5R)-3-acetoxy-5-(6-chloro-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate (1187433-96-0) + ((2R,3S,4R,5S)-3-acetoxy-5-(6-chloro-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate (1187434-00-9)

Guidance literature:

6-chloro-7H-purine; With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 0 ℃;

(3R,4S,5R)-5-(benzoyloxymethyl)-3-fluoro-3,4-dimethyltetrahydrofuran-2,4-diyl diacetate; In acetonitrile; at 0 - 65 ℃;

Reference yield:

(3R,4S,5R)-5-(benzoyloxymethyl)-3-fluoro-3,4-dimethyltetrahydrofuran-2,4-diyl diacetate (1187433-95-9) + 6-chloropurine (87-42-3) → ((2R,3S,4R,5R)-3-acetoxy-5-(6-chloro-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate (1187433-96-0) + ((2R,3S,4R,5S)-3-acetoxy-5-(6-chloro-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate (1187434-00-9)

Guidance literature:

6-chloropurine; With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 0 ℃; for 0.25h; Inert atmosphere;

(3R,4S,5R)-5-(benzoyloxymethyl)-3-fluoro-3,4-dimethyltetrahydrofuran-2,4-diyl diacetate; In acetonitrile; at 0 - 65 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2010.07.017

Reference yield: 62.0%

((2R,3S,4R,5S)-3-acetoxy-5-(6-chloro-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate (1187434-00-9) + Cyclopropylamine (765-30-0) → ((2R,3S,4R,5S)-3-acetoxy-5-(6-(cyclopropylamino)-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate (1187434-70-3)

Guidance literature:

In ethanol; for 0.5h; Reflux; Inert atmosphere;

DOI:10.1016/j.bmc.2010.07.017

upstream raw materials:

(3R,4S,5R)-5-(benzoyloxymethyl)-3-fluoro-3,4-dimethyltetrahydrofuran-2,4-diyl diacetate

6-chloro-7H-purine

6-chloropurine

Downstream raw materials:

((2R,3S,4R,5S)-3-acetoxy-4-fluoro-3,4-dimethyl-5-(6-morpholino-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl benzoate

((2R,3S,4R,5S)-3-acetoxy-4-fluoro-3,4-dimethyl-5-(6-(4-methylpiperazin-1-yl)-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl benzoate

((2R,3S,4R,5S)-3-acetoxy-4-fluoro-5-(6-(furan-2-ylmethylamino)-9H-purin-9-yl)-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate

((2R,3S,4R,5S)-3-acetoxy-4-fluoro-3,4-dimethyl-5-(6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-2-yl)methyl benzoate

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