9-((1S,3R,4R)-3,4-Bis-benzyloxymethyl-3-fluoro-cyclopentyl)-6-chloro-9H-purin-2-ylamine

Base Information

• Chemical Name: 9-((1S,3R,4R)-3,4-Bis-benzyloxymethyl-3-fluoro-cyclopentyl)-6-chloro-9H-purin-2-ylamine
• CAS No.: 246518-33-2
• Molecular Formula: C₂₆H₂₇ClFN₅O₂
• Molecular Weight: 495.984
• Mol file: 246518-33-2.mol

Synonyms:9-((1S,3R,4R)-3,4-Bis-benzyloxymethyl-3-fluoro-cyclopentyl)-6-chloro-9H-purin-2-ylamine

Chemical Property of 9-((1S,3R,4R)-3,4-Bis-benzyloxymethyl-3-fluoro-cyclopentyl)-6-chloro-9H-purin-2-ylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-((1S,3R,4R)-3,4-Bis-benzyloxymethyl-3-fluoro-cyclopentyl)-6-chloro-9H-purin-2-ylamine

There total 12 articles about 9-((1S,3R,4R)-3,4-Bis-benzyloxymethyl-3-fluoro-cyclopentyl)-6-chloro-9H-purin-2-ylamine 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%

2-Amino-6-chloropurin (10310-21-1) + (1R,3R,4R)-3,4-bis(benzyloxymethyl)-4-fluoro-1-cyclopentanol (246518-31-0) → 9-((1S,3R,4R)-3,4-Bis-benzyloxymethyl-3-fluoro-cyclopentyl)-6-chloro-9H-purin-2-ylamine (246518-33-2)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 15h;

DOI:10.1016/S0040-4020(99)00591-8

Reference yield:

benzyl bromide (100-39-0) → 9-((1S,3R,4R)-3,4-Bis-benzyloxymethyl-3-fluoro-cyclopentyl)-6-chloro-9H-purin-2-ylamine (246518-33-2)

Guidance literature:

Multi-step reaction with 11 steps

1: tetrabutylammonium hydrogen sulfate; Et₃N; NaOH / CH₂Cl₂; H₂O / 40 h / Heating

2: 5.58 g / p-TsOH; H₂O / dioxane / 1.3 h / 70 °C

3: 81 percent / Me₄NBH(OAc)3; AcOH / acetone; acetonitrile / 48 h / 20 °C

4: 91 percent / ICH₂CH₂I; PPh₃ / tetrahydrofuran / 144 h

5: 76 percent / DBU / toluene / 18 h / 95 °C

6: 90 percent / DMAP; Et₃N / CH₂Cl₂ / 72 h / Heating

7: 66 percent / K₂OsO₄*2H₂O; 4-methylmorpholine N-oxide / tetrahydrofuran; H₂O / 24 h / 20 °C

8: 87 percent / NaH / dimethylformamide / 20 h / -78 - 20 °C

9: Deoxofluor; pyridine / CH₂Cl₂ / 18 h / -78 - 20 °C

10: 83 mg / pTsOH; H₂O / CH₂Cl₂ / 2.5 h / 20 °C

11: 82 percent / DIAD; PPh₃ / tetrahydrofuran / 15 h / 20 °C

With pyridine; dmap; sodium hydroxide; potassium osmate(VI); 1,2-Diiodoethane; di-isopropyl azodicarboxylate; water; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; (bis-(2-methoxyethyl)amino)sulfur trufluoride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 1: Etherification / 2: Hydrolysis / 3: Reduction / 4: Iodination / 5: Elimination / 6: Etherification / 7: dihydroxylation / 8: Etherification / 9: Fluorination / 10: Hydrolysis / 11: Mitsunobu reaction;

DOI:10.1016/S0040-4020(99)00591-8

Reference yield:

(3S,4S)-bis(hydroxymethyl)cyclopentanone ethylene glycol ketal (246518-20-7) → 9-((1S,3R,4R)-3,4-Bis-benzyloxymethyl-3-fluoro-cyclopentyl)-6-chloro-9H-purin-2-ylamine (246518-33-2)

Guidance literature:

Multi-step reaction with 11 steps

1: tetrabutylammonium hydrogen sulfate; Et₃N; NaOH / CH₂Cl₂; H₂O / 40 h / Heating

2: 5.58 g / p-TsOH; H₂O / dioxane / 1.3 h / 70 °C

3: 81 percent / Me₄NBH(OAc)3; AcOH / acetone; acetonitrile / 48 h / 20 °C

4: 91 percent / ICH₂CH₂I; PPh₃ / tetrahydrofuran / 144 h

5: 76 percent / DBU / toluene / 18 h / 95 °C

6: 90 percent / DMAP; Et₃N / CH₂Cl₂ / 72 h / Heating

7: 66 percent / K₂OsO₄*2H₂O; 4-methylmorpholine N-oxide / tetrahydrofuran; H₂O / 24 h / 20 °C

8: 87 percent / NaH / dimethylformamide / 20 h / -78 - 20 °C

9: Deoxofluor; pyridine / CH₂Cl₂ / 18 h / -78 - 20 °C

10: 83 mg / pTsOH; H₂O / CH₂Cl₂ / 2.5 h / 20 °C

11: 82 percent / DIAD; PPh₃ / tetrahydrofuran / 15 h / 20 °C

With pyridine; dmap; sodium hydroxide; potassium osmate(VI); 1,2-Diiodoethane; di-isopropyl azodicarboxylate; water; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; (bis-(2-methoxyethyl)amino)sulfur trufluoride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 1: Etherification / 2: Hydrolysis / 3: Reduction / 4: Iodination / 5: Elimination / 6: Etherification / 7: dihydroxylation / 8: Etherification / 9: Fluorination / 10: Hydrolysis / 11: Mitsunobu reaction;

DOI:10.1016/S0040-4020(99)00591-8

upstream raw materials:

2-Amino-6-chloropurin

(1R,3R,4R)-3,4-bis(benzyloxymethyl)-4-fluoro-1-cyclopentanol

benzyl bromide

(3S,4S)-bis(hydroxymethyl)cyclopentanone ethylene glycol ketal