Cladribine impurity D [EP IMPURITY]

Base Information

• Chemical Name: Cladribine impurity D [EP IMPURITY]
• CAS No.: 5542-92-7
• Molecular Formula: C10H12ClN5O3
• Molecular Weight: 285.69
• UNII: P44J6L6VZ7
• Nikkaji Number: J585.326E
• ChEMBL ID: CHEMBL4776881
• Mol file: 5542-92-7.mol

Synonyms:1'-epi-Cladribine;P44J6L6VZ7;Cladribine impurity D [EP IMPURITY];NSC-105013;2-Chloro-9-(2-deoxy-alpha-D-erythro-pentofuranosyl)-9H-purin-6-amine;NCIMech_000407;UNII-P44J6L6VZ7;SCHEMBL2789344;CHEMBL4776881;2-Chloro-alpha-D-2'-deoxyadenosine;CCG-35507;2-CHLORO-.ALPHA.-D-2'-DEOXYADENOSINE;Adenine, 2-chloro-9-(2-deoxy-alpha-D-erythro-pentofuranosyl)-;2-Chloro-6-amino-9-(2-deoxy-alpha-D-erythro-pentofuranosyl)purine;9H-Purin-6-amine, 2-chloro-9-(2-deoxy-alpha-D-erythro-pentofuranosyl)-;ADENINE, 2-CHLORO-9-(2-DEOXY-.ALPHA.-D-ERYTHRO-PENTOFURANOSYL)-;(2R,3S,5S)-5-(6-Amino-2-chloro-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol;2-CHLORO-6-AMINO-9-(2-DEOXY-.ALPHA.-D-ERYTHRO-PENTOFURANOSYL)PURINE;2-CHLORO-9-(2-DEOXY-.ALPHA.-D-ERYTHRO-PENTOFURANOSYL)-9H-PURIN-6-AMINE;9H-PURIN-6-AMINE, 2-CHLORO-9-(2-DEOXY-.ALPHA.-D-ERYTHRO-PENTOFURANOSYL)-

Chemical Property of Cladribine impurity D [EP IMPURITY]

Chemical Property:

• Boiling Point: 547.6°Cat760mmHg
• Flash Point: 285°C
• Density: 2.03g/cm³
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 285.0628670
• Heavy Atom Count: 19
• Complexity: 338

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=NC3=C(N=C(N=C32)Cl)N)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@@H]1N2C=NC3=C(N=C(N=C32)Cl)N)CO)O

Technology Process of Cladribine impurity D [EP IMPURITY]

There total 5 articles about Cladribine impurity D [EP IMPURITY] 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: 70.0%

2-chloro-9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-(2-pentylimidazol-1-yl)purine (914084-44-9) → 6-amino-2-chloro-9-(2-deoxy-α-D-erythro-pentofuranosyl)purine (5542-92-7) + 2-chloro-2'-deoxyadenosine (4291-63-8)

Guidance literature:

With ammonia; In methanol; at 80 ℃; for 13h;

Reference yield:

2-chloro-6-(4-oxopyridin-1-yl)-[2'-deoxy-3',5'-di-O-(p-toluoyl)-α/β-D-erythro-pentofuranosyl]purine → 6-amino-2-chloro-9-(2-deoxy-α-D-erythro-pentofuranosyl)purine (5542-92-7) + 2-chloro-2'-deoxyadenosine (4291-63-8)

Guidance literature:

With ammonia; In methanol; at 60 ℃; for 63h; Overall yield = 61 %; Overall yield = 0.29 g; Sealed tube;

Reference yield:

2-chloro-6-(4-oxo-3,5-diphenylpyridin-1-yl)-[2′-deoxy-3′,5′-di-O-(p-toluoyl)-α/β-D-erythro-pentofuranosyl]purine → 6-amino-2-chloro-9-(2-deoxy-α-D-erythro-pentofuranosyl)purine (5542-92-7) + 2-chloro-2'-deoxyadenosine (4291-63-8)

Guidance literature:

With ammonia; In methanol; at 60 ℃; for 63h; Sealed tube;

upstream raw materials:

2-chloro-9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-(2-pentylimidazol-1-yl)purine

Refernces

• 1、 -. "METHODS FOR SELECTIVE N-9 GLYCOSYLATION OF PURINES". Page/Page column 61. . Retrieved 2010/11/25.