3056-18-6

Usage

Chemical Properties

Off-White to Pale Yellow Solid

Uses

Protected nucleoside.

InChI:InChI=1/C16H16Cl2N4O7/c1-6(23)26-4-9-11(27-7(2)24)12(28-8(3)25)15(29-9)22-5-19-10-13(17)20-16(18)21-14(10)22/h5,9,11-12,15H,4H2,1-3H3

Upstream product

• 16321-99-6 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 

Downstream Products

• 23559-45-7 (2R,3R,4S,5R)-2-[2-Chloro-6-((S)-1-methyl-2-phenyl-ethylamino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 23558-58-9 2-chloro-N-<1-phenyl-2(R)-propyl>-9-β-D-ribofuranosyl-9H-purin-6-amine 
• 146-77-0 2-Chloroadenosine 
• 79999-39-6 2',3',5'-tri-O-acetyl-2-chloroadenosine 
• 98383-72-3 2-Chloro-N-(2,2-diphenylethyl)-adenosine 2',3',5'-triacetate 
• 38583-85-6 2-chloro-N⁶-cyclohexyladenosine 
• 149007-83-0 6-cyclopropylamino-2-chloro-9-(β-D-ribofuranosyl)purine 
• 891497-95-3 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-chloro-6-(4,5-diphenylimidazol-1-yl)purine 
• 920974-75-0 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(2-chloro-6-(cyclohexylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 891497-96-4 2-chloro-6-(4,5-diphenylimidazol-1-yl)purine 
• 41552-82-3 N-cyclopentyladenosine 
• 41552-83-4 N6-Cycloheptyladenosine 
• 41552-84-5 N6-Cyclooctyladenosine 
• 36396-99-3 N₆-cyclohexyladenosine 

Relevant academic research and scientific papers

Anti-HCV nucleoside derivatives

The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

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%).