[(1S,4R)-4-(2-Amino-6-chloro-purin-9-yl)-1-benzyl-cyclopent-2-enyl]-methanol

Base Information

• Chemical Name: [(1S,4R)-4-(2-Amino-6-chloro-purin-9-yl)-1-benzyl-cyclopent-2-enyl]-methanol
• CAS No.: 206755-15-9
• Molecular Formula: C₁₈H₁₈ClN₅O
• Molecular Weight: 355.827
• Mol file: 206755-15-9.mol

Synonyms:

Chemical Property of [(1S,4R)-4-(2-Amino-6-chloro-purin-9-yl)-1-benzyl-cyclopent-2-enyl]-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,4R)-4-(2-Amino-6-chloro-purin-9-yl)-1-benzyl-cyclopent-2-enyl]-methanol

There total 19 articles about [(1S,4R)-4-(2-Amino-6-chloro-purin-9-yl)-1-benzyl-cyclopent-2-enyl]-methanol 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:

methyl (1RS)-2,2-((R,R)-cycloheptane-1,2-dioxy)cyclopentanecarboxylate (206760-76-1) → [(1S,4R)-4-(2-Amino-6-chloro-purin-9-yl)-1-benzyl-cyclopent-2-enyl]-methanol (206755-15-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 90 percent / LDA

2: 99 percent / I₂, Et₃N / tetrahydrofuran / 12 h / -40 °C

3: 95 percent / DBU / 1 h / 95 - 100 °C

4: LiAlH₄ / tetrahydrofuran

5: 10percent HCl / methanol

6: 70 percent / NaBH₄, CeCl₃

7: 80 percent / DMAP

8: imidazole

9: 90 percent / KOH / methanol

10: Ph₃P, EtO₂CN=NCO₂Et

11: TBAF

With 1H-imidazole; hydrogenchloride; dmap; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; tetrabutyl ammonium fluoride; iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol;

DOI:10.1016/S0957-4166(98)00065-2

Reference yield:

methyl 2-oxocyclopentane-1-carboxylate (10472-24-9,265317-94-0) → [(1S,4R)-4-(2-Amino-6-chloro-purin-9-yl)-1-benzyl-cyclopent-2-enyl]-methanol (206755-15-9)

Guidance literature:

Multi-step reaction with 12 steps

1: TsOH

2: 90 percent / LDA

3: 99 percent / I₂, Et₃N / tetrahydrofuran / 12 h / -40 °C

4: 95 percent / DBU / 1 h / 95 - 100 °C

5: LiAlH₄ / tetrahydrofuran

6: 10percent HCl / methanol

7: 70 percent / NaBH₄, CeCl₃

8: 80 percent / DMAP

9: imidazole

10: 90 percent / KOH / methanol

11: Ph₃P, EtO₂CN=NCO₂Et

12: TBAF

With 1H-imidazole; hydrogenchloride; dmap; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; tetrabutyl ammonium fluoride; iodine; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol;

DOI:10.1016/S0957-4166(98)00065-2

Reference yield:

(1S,5S)-5-benzyl-5-hydroxymethyl-2-cyclopentenol (249536-90-1) → [(1S,4R)-4-(2-Amino-6-chloro-purin-9-yl)-1-benzyl-cyclopent-2-enyl]-methanol (206755-15-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / DMAP

2: imidazole

3: 90 percent / KOH / methanol

4: Ph₃P, EtO₂CN=NCO₂Et

5: TBAF

With 1H-imidazole; dmap; potassium hydroxide; tetrabutyl ammonium fluoride; triphenylphosphine; diethylazodicarboxylate; In methanol;

DOI:10.1016/S0957-4166(98)00065-2

upstream raw materials:

methyl (1RS)-2,2-((R,R)-cycloheptane-1,2-dioxy)cyclopentanecarboxylate

methyl 2-oxocyclopentane-1-carboxylate

2-Amino-6-chloropurin

(1S,5S)-5-benzyl-5-hydroxymethyl-2-cyclopentenol