Acetic acid (1S,2R,4R)-4-(6-acetylamino-purin-9-yl)-2-trityloxymethyl-cyclopentyl ester

Base Information

• Chemical Name: Acetic acid (1S,2R,4R)-4-(6-acetylamino-purin-9-yl)-2-trityloxymethyl-cyclopentyl ester
• CAS No.: 201848-24-0
• Molecular Formula: C₃₄H₃₃N₅O₄
• Molecular Weight: 575.667

Synonyms:Acetic acid (1S,2R,4R)-4-(6-acetylamino-purin-9-yl)-2-trityloxymethyl-cyclopentyl ester

Chemical Property of Acetic acid (1S,2R,4R)-4-(6-acetylamino-purin-9-yl)-2-trityloxymethyl-cyclopentyl ester

Chemical Property:

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Technology Process of Acetic acid (1S,2R,4R)-4-(6-acetylamino-purin-9-yl)-2-trityloxymethyl-cyclopentyl ester

There total 5 articles about Acetic acid (1S,2R,4R)-4-(6-acetylamino-purin-9-yl)-2-trityloxymethyl-cyclopentyl 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: 78.8%

acetic anhydride (108-24-7) + (1S,2R,4R)-4-(6-Amino-purin-9-yl)-2-trityloxymethyl-cyclopentanol (201861-92-9) → Acetic acid (1S,2R,4R)-4-(6-acetylamino-purin-9-yl)-2-trityloxymethyl-cyclopentyl ester (201848-24-0)

Guidance literature:

With dmap; In pyridine; at 25 ℃; for 40h;

DOI:10.1080/07328319708002566

Reference yield:

6-chloropurine (87-42-3) → Acetic acid (1S,2R,4R)-4-(6-acetylamino-purin-9-yl)-2-trityloxymethyl-cyclopentyl ester (201848-24-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / PPh₃, DEAD / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) 25 deg C, 16 h

2: 99 percent / NH₃ (liq) / methanol; acetone / 24 h / 70 °C

3: 92.9 percent / TBAF / tetrahydrofuran / 20 h / 25 °C

4: 78.8 percent / DMAP / pyridine / 40 h / 25 °C

With dmap; tetrabutyl ammonium fluoride; ammonia; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; pyridine; methanol; acetone;

DOI:10.1080/07328319708002566

Reference yield:

(1S,3S,4R)-3-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-trityloxymethyl-cyclopentanol (167260-21-1) → Acetic acid (1S,2R,4R)-4-(6-acetylamino-purin-9-yl)-2-trityloxymethyl-cyclopentyl ester (201848-24-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / PPh₃, DEAD / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) 25 deg C, 16 h

2: 99 percent / NH₃ (liq) / methanol; acetone / 24 h / 70 °C

3: 92.9 percent / TBAF / tetrahydrofuran / 20 h / 25 °C

4: 78.8 percent / DMAP / pyridine / 40 h / 25 °C

With dmap; tetrabutyl ammonium fluoride; ammonia; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; pyridine; methanol; acetone;

DOI:10.1080/07328319708002566

upstream raw materials:

acetic anhydride

(1S,2R,4R)-4-(6-Amino-purin-9-yl)-2-trityloxymethyl-cyclopentanol

6-chloropurine

(1S,3S,4R)-3-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-trityloxymethyl-cyclopentanol

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