461003-95-2

Basic information

• Product Name: 1-β-D-(3,5-O-tetraisopropyldisilyloxy-2-O-trifluoromethanesulfonylribofuranosyl)-2-nitroimidazole
• Synonyms: 1-β-D-(3,5-O-tetraisopropyldisilyloxy-2-O-trifluoromethanesulfonylribofuranosyl)-2-nitroimidazole
• CAS NO: 461003-95-2
• Molecular Weight: 619.764
• Mol File: 461003-95-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-β-D-(3,5-O-tetraisopropyldisilyloxy-2-O-trifluoromethanesulfonylribofuranosyl)-2-nitroimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-β-D-(3,5-O-tetraisopropyldisilyloxy-2-O-trifluoromethanesulfonylribofuranosyl)-2-nitroimidazole(461003-95-2)
• EPA Substance Registry System: 1-β-D-(3,5-O-tetraisopropyldisilyloxy-2-O-trifluoromethanesulfonylribofuranosyl)-2-nitroimidazole(461003-95-2)

Safety Data

• Hazardous Substances Data: 461003-95-2(Hazardous Substances Data)

Upstream product

• 18043-71-5 1,1,3,3-tetraisopropyldisiloxane 

Downstream Products

• 639079-80-4 1-β-[2',3'-di-O-acetyl-5'-(tert-butyldiphenylsilyl)-D-arabinofuranosyl]-2-nitroimidazole 
• 475570-49-1 1-β-D-[5-O-toluenesulfonyl-2,3-di-O-acetylarabinofuranosyl]-2-nitroimidazole 
• 639079-78-0 1-β-D-[5-O-toluenesulfonyl-2-O-acetyl-arabinofuranosyl]-2-nitroimidazole 

Relevant articles and documents

Synthesis of β-azomycin nucleosides: 1-(β-D-2-iodo-2-deoxyarabinofuranosyl)-2-nitroimidazole (β-2-IAZA), a novel marker of tissue hypoxia

This study describes a non-conventional approach to the synthesis of 1-β-D-[2-deoxy-2-iodoarabinofuranosyl]-2-nitroimidazole (β-2-IAZA), a positional and configurational isomer of 1-α-D-[5-deoxy-5-iodoarabinofuranosyl]-2-nitroimidazole (IAZA). [123I]IAZA, a radiopharmaceutical used clinically to image regional tissue hypoxia in a number of pathologies, is synthesized by coupling the appropriately protected 1-α-halo arabinofuranoside, with azomycin, with retention of configuration. To circumvent participation of the C-2′ protecting group, which prevents β-anomer formation during coupling, the riboside 1-β-D-(ribofuranosyl)-2-nitroimidazole (AZR) was elaborated to 1-β-D-(3,5-tetraisopropyldisylyloxy-2-O- trifluoromethanesulfonylribofuranosyl)-2-nitroimidazole. Nucleophilic displacement of the 2-O-trifluoromethanesulfonyl leaving group by iodide results in inversion of configuration at the ribosyl C-2-position, thereby affording silylated arabinofuranosyl-2′-IAZA, which was desilylated under neutral conditions to afford β-2-IAZA.