156517-72-5

Basic information

• Product Name: 6-chloro-9-(3,5-bis-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)purine
• Synonyms: 6-chloro-9-(3,5-bis-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)purine
• CAS NO: 156517-72-5
• Molecular Weight: 354.75
• Mol File: 156517-72-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 6-chloro-9-(3,5-bis-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)purine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-9-(3,5-bis-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)purine(156517-72-5)
• EPA Substance Registry System: 6-chloro-9-(3,5-bis-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)purine(156517-72-5)

Safety Data

• Hazardous Substances Data: 156517-72-5(Hazardous Substances Data)

Upstream product

• 17318-24-0 3',5'-di-O-acetyl-2'-deoxyadenosine 

Downstream Products

• 16006-64-7 6-methyl-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine 
• 35665-58-8 N⁶,N⁶-dimethyl-2'-deoxyadenosine 
• 4594-45-0 6-chloropurine-2'-deoxyriboside 

Relevant articles and documents

Nucleic acid related compounds. 118. Nonaqueous diazotization of aminopurine derivatives. Convenient access to 6-halo- and 2,6-dihalopurine nucleosides and 2′-deoxynucleosides with acyl or silyl halides

Treatment of 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-chloropurine (1) with TMS-Cl and benzyltriethylammonium nitrite (BTEA-NO2) in dichloromethane gave the crystalline 2,6-dichloropurine nucleoside 2, and acetyl chloride/BTEA-NO2 was equally effective (～85%, without chromatography). TMS-Br/tert-butyl nitrite/dibromomethane gave crystalline 2-bromo-6-chloro analogue 3 (85%). (Chloro or bromo)-dediazoniation of 3′,5′-di-O-acetyl-2′-deoxyadenosine (4) gave the 6-[chloro (5, 63%) or bromo (6, 80%)]purine deoxynucleosides, and 2′,3′,5′-tri-O-acetyladenosine (8) was converted into the 6-chloropurine nucleoside 9 (71%).