87190-83-8

Basic information

• Product Name: 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-iodouracil
• Synonyms: 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-iodouracil
• CAS NO: 87190-83-8
• Molecular Weight: 621.434
• Mol File: 87190-83-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-iodouracil(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-iodouracil(87190-83-8)
• EPA Substance Registry System: 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-iodouracil(87190-83-8)

Safety Data

• Hazardous Substances Data: 87190-83-8(Hazardous Substances Data)

Upstream product

• 84472-85-5 Navuridine 
• 101039-82-1 5-iodo-3'-O-mesyl-5'-O-trityl-2'-deoxyuridine 
• 101039-85-4 2,3'-anydro-5-iodo-5'-O-trityl-2'-deoxyuridine 
• 76-83-5 trityl chloride 
• 85236-92-6 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-iodouracil 

Downstream Products

• 85236-92-6 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-iodouracil 
• 87190-89-4 1-((2R,4S,5S)-4-Azido-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione 

Relevant articles and documents

Synthesis and biological activity of 3'-azido- and 3'-amino substituted nucleoside analogs

The product distribution obtained in the reaction of 1-(5-0-trityl-0-mesyl-2-deoxy-β-D-erythro-pentofuranosyl)-2,4-(1H, 3H)-pyrimidinedione with lithium azide in N, N'-dimethylformamide at 100°C depends on the nature of the substituent in 5. The results may be explained by a difference in the acidity of the pyrimidinedione. The reaction of the more acidic nucleosides (X = I, F) appears to proceed preferentially through the 2,3'-anhydro intermediate, whereas for the less acidic products (X = H, CH3) direct nucleophilic displacement by the azide ion predominates. The different 3'-azidfo derivatives were reduced to 3'-amino compounds. All 3'-azido- and 3'-aminopyrimidine nucleosides were tested against herpes simplex virus, vaccinia and vesicular stomatitis virus and on murine L1210 cell growth. None of the substances exhibited significant activity.