(3R,4S,5R)-2-[6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

Base Information

• Chemical Name: (3R,4S,5R)-2-[6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS No.: 41552-82-3
• Molecular Formula: C15H21N5O4
• Molecular Weight: 335.36
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID80961807
• Mol file: 41552-82-3.mol

Synonyms:SCHEMBL12200134;DTXSID80961807;PD057690

Chemical Property of (3R,4S,5R)-2-[6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

Chemical Property:

• Vapor Pressure: 4.71E-19mmHg at 25°C
• Refractive Index: 1.816
• Boiling Point: 673.4 °C at 760 mmHg
• PKA: 13.12±0.70(Predicted)
• Flash Point: 361.1 °C
• PSA: 125.55000
• Density: 1.78 g/cm³
• LogP: -0.13470
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble1.7mg/mL
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 335.15935417
• Heavy Atom Count: 24
• Complexity: 438

Purity/Quality:

97% ^*data from raw suppliers

N6-Cyclopentyladenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C1)NC2=C3C(=NC=N2)N(C=N3)C4C(C(C(O4)CO)O)O
• Isomeric SMILES: C1CCC(C1)NC2=C3C(=NC=N2)N(C=N3)C4[C@@H]([C@@H]([C@H](O4)CO)O)O
• Uses: N6-Cyclopentyladenosine is a selective Adenosine A1-R agonist with Ki values of 2.3, 790 and 43 nM for human A1, A2A and A3 receptors respectively and EC50 value of 18600 nM for hA2B. It has also shown its efficacy against organophosphate toxcity. N6-Cyclopentyladenosine has been used to study its effect on the cavernosal smooth muscle cells from lean and db/db (obesity and type II diabetes caused by a leptin receptor mutation) mice.

Technology Process of (3R,4S,5R)-2-[6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

There total 10 articles about (3R,4S,5R)-2-[6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol 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: 85.0%

C42H47N5O6 (1229622-80-3) → N-cyclopentyladenosine (41552-82-3)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; at 55 ℃; for 72h;

DOI:10.1016/j.tetlet.2010.03.103

Reference yield: 80.0%

6-Iodo-purine riboside (14426-53-0) + Cyclopentamine (1003-03-8) → N-cyclopentyladenosine (41552-82-3)

Guidance literature:

for 1h;

DOI:10.12659/MSM.902048

Reference yield: 79.0%

6-Chloropurine riboside (2004-06-0) + Cyclopentamine (1003-03-8) → N-cyclopentyladenosine (41552-82-3)

Guidance literature:

With triethylamine; In ethanol; at 80 ℃; for 3h;

DOI:10.1016/j.bmc.2010.09.030

upstream raw materials:

6-Chloropurine riboside

Cyclopentamine

2-chloro-N⁶-cyclopentyladenosine

(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate

Downstream raw materials:

cyclohexanecarboxylic acid 6-(6-cyclopentylamino-purin-9-yl)-2-ethoxy-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester

3,4,5-trimethoxy-benzoic acid 6-(6-cyclopentylamino-purin-9-yl)-2-ethoxy-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester

Cyclopentyl-{9-[(3aR,4R,6S,6aS)-6-(2-fluoro-phenylsulfanylmethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-amine

(2R,3R,4R,5S)-4-Azido-2-(6-cyclopentylamino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3-ol