(2R,3R,4R,5R)-2-(6-(Cyclopentylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-(6-(Cyclopentylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol
• CAS No.: 205171-06-8
• Molecular Formula: C₁₆H₂₃N₅O₄
• Molecular Weight: 349.39
• DSSTox Substance ID: DTXSID90433207
• Nikkaji Number: J962.606I
• Wikidata: Q72460478
• Pharos Ligand ID: BN7MZSLVR2YX
• ChEMBL ID: CHEMBL400189
• Mol file: 205171-06-8.mol

Synonyms:205171-06-8;N-Cyclopentyl-2'-C-methyl-adenosine;(2R,3R,4R,5R)-2-(6-(Cyclopentylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol;Adenosine, N-cyclopentyl-2'-C-methyl-;CHEMBL400189;(2R,3R,4R,5R)-2-[6-(CYCLOPENTYLAMINO)PURIN-9-YL]-5-(HYDROXYMETHYL)-3-METHYLOXOLANE-3,4-DIOL;SCHEMBL6382804;DTXSID90433207;N-Cyclopentyl-2'-methyladenosine;BVOLJUDYJILMMW-QTDMDRALSA-N;BDBM50224775;AC-32332;BS-50103;E78015;A879584;9-(2'-C-methyl-beta-D-ribofuranosyl)-6-(cyclopentylamino)purine;(2R,3R,4R,5R)-2-(6-(cyclopentylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol;(2R,3R,4R,5R)-2-[6-(cyclopentylamino)-9H-purin-9-yl]-5-(hydroxymethyl)-3-methyloxolane-3,4-diol

Chemical Property of (2R,3R,4R,5R)-2-(6-(Cyclopentylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol

Chemical Property:

• PSA: 125.55000
• Density: 1.67
• LogP: 0.25540
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 349.17500423
• Heavy Atom Count: 25
• Complexity: 479

Purity/Quality:

98%,99%, ^*data from raw suppliers

N6-Cyclopentyl-2'-C-methyl-adenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(C(OC1N2C=NC3=C(N=CN=C32)NC4CCCC4)CO)O)O
• Isomeric SMILES: C[C@]1([C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)NC4CCCC4)CO)O)O

Technology Process of (2R,3R,4R,5R)-2-(6-(Cyclopentylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol

There total 6 articles about (2R,3R,4R,5R)-2-(6-(Cyclopentylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-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: 60.0%

Cyclopentamine (1003-03-8) + 6-chloro-9-(2-C-methyl-?2-D-ribofuranosyl)-9H-purine (205171-05-7) → 2'-Me-CPA (205171-06-8)

Guidance literature:

In ethanol; for 5h; Heating;

DOI:10.1021/jm9707737

Reference yield:

C37H35N5O7 → 2'-Me-CPA (205171-06-8)

Guidance literature:

With ammonia; In methanol; at 20 ℃;

DOI:10.1021/jm801456g

Reference yield:

6-chloropurine (87-42-3) → 2'-Me-CPA (205171-06-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / DBU, Me₃SiOTf / acetonitrile / 4 h / 60 °C

2: 72 percent / methanolic NH₃ / 7 h / Ambient temperature

3: 60 percent / ethanol / 5 h / Heating

With trimethylsilyl trifluoromethanesulfonate; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; acetonitrile;

DOI:10.1021/jm9707737

upstream raw materials:

Cyclopentamine

6-chloro-9-(2-C-methyl-?2-D-ribofuranosyl)-9H-purine

6-chloropurine

1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose

Refernces

• 1、 -. "NUCLEOSIDE DERIVATIVES FOR TREATING HEPATITIS C VIRUS INFECTION". Page/Page column 113. . Retrieved 2010/02/07.