(1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enol

Base Information

• Chemical Name: (1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enol
• CAS No.: 133119-17-2
• Molecular Formula: C₁₈H₂₀N₆O₂
• Molecular Weight: 352.396
• Mol file: 133119-17-2.mol

Synonyms:(1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enol

Chemical Property of (1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enol

There total 3 articles about (1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enol 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:

(2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol (117641-39-1) → (1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enol (133119-17-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / 4-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

2: Bu₄NF / tetrahydrofuran / 72 h / Ambient temperature

3: 1) NaH, 2) 15-crown-5 / 1) DMF, 85 deg C, 20 min, 2) DMF, 100 deg C, 3 h

With dmap; 15-crown-5; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/P19910002479

Reference yield:

(1S,2R,3S,5R)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ylmethanesulphonate (133119-15-0) → (1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enol (133119-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Bu₄NF / tetrahydrofuran / 72 h / Ambient temperature

2: 1) NaH, 2) 15-crown-5 / 1) DMF, 85 deg C, 20 min, 2) DMF, 100 deg C, 3 h

With 15-crown-5; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran;

DOI:10.1039/P19910002479

Reference yield:

(1S,2S,5R)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hex-3-ene (133119-16-1) + 2,6-diaminopurine (1904-98-9) → (1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enol (133119-17-2)

Guidance literature:

With 15-crown-5; sodium hydride; Yield given. Multistep reaction; 1) DMF, 85 deg C, 20 min, 2) DMF, 100 deg C, 3 h;

DOI:10.1039/P19910002479

upstream raw materials:

(1S,2S,5R)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hex-3-ene

2,6-diaminopurine

(2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol

(1S,2R,3S,5R)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ylmethanesulphonate

Downstream raw materials:

(1'R,4'S)-9-(4-benzyloxymethylcyclopent-2-enyl)-9H-purine-2,6-diamine

(1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enylphenoxythiocarboxylate