500225-60-5

Basic information

• Product Name: Inosine, 2-chloro-2'-deoxy-, 3',5'-dibenzoate 6-(4-methylbenzenesulfonate)
• CAS NO: 500225-60-5
• Molecular Formula: C31H25ClN4O8S
• Molecular Weight: 649.08
• Mol File: 500225-60-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Inosine, 2-chloro-2'-deoxy-, 3',5'-dibenzoate 6-(4-methylbenzenesulfonate)(CAS DataBase Reference)
• NIST Chemistry Reference: Inosine, 2-chloro-2'-deoxy-, 3',5'-dibenzoate 6-(4-methylbenzenesulfonate)(500225-60-5)
• EPA Substance Registry System: Inosine, 2-chloro-2'-deoxy-, 3',5'-dibenzoate 6-(4-methylbenzenesulfonate)(500225-60-5)

Safety Data

• Hazardous Substances Data: 500225-60-5(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 59921-49-2 3',5'-di-O-benzoyl-2'-deoxyguanosine 
• 500225-57-0 2-amino-9-(3,5-di-O-benzoyl-2-deoxy-β-D-erythro-pentofuranosyl)-6-O-(4-methylbenzenesulfonyl)purine 

Downstream Products

• 4291-63-8 2-chloro-2'-deoxyadenosine 

Relevant articles and documents

Efficient syntheses of 2-chloro-2′-deoxyadenosine (cladribine) from 2′-deoxyguanosine

We report efficient syntheses of the clinical agent cladribine (2-chloro-2′-deoxyadenosine, CldAdo), which is the drug of choice against hairy-cell leukemia and other neoplasms, from 2′-deoxyguanosine. Treatment of 3′,5′-di-O-acetyl- or benzoyl-2′-deoxyguanosine (1) with 2,4,6-triisopropyl- or 4-methylbenzenesulfonyl chloride gave high yields of the 6-O-arylsulfonyl derivatives 2 or 2′b. Deoxychlorination at C6 of 1 also proceeded to give the 2-amino-6-chloropurine derivative 5 in excellent yields. The nonaqueous diazotization/chloro dediazoniation (acetyl chloride/benzyltriethylammonium nitrite) of 2, 2′b, and 5 gave the 2-chloropurine derivatives 3, 3′b, and 6, respectively. The selective ammonolysis at C6 (arylsulfonate with 3 or chloride with 6) and accompanying deprotection of the sugar moiety gave CldAdo (64-75% overall yield from 1).