18892-65-4

Basic information

• Product Name: 2,3'-anhydro-1-(2-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)-5-fluorouracil
• Synonyms: 2,3'-anhydro-1-(2-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)-5-fluorouracil
• CAS NO: 18892-65-4
• Molecular Weight: 470.5
• Mol File: 18892-65-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,3'-anhydro-1-(2-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)-5-fluorouracil(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3'-anhydro-1-(2-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)-5-fluorouracil(18892-65-4)
• EPA Substance Registry System: 2,3'-anhydro-1-(2-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)-5-fluorouracil(18892-65-4)

Safety Data

• Hazardous Substances Data: 18892-65-4(Hazardous Substances Data)

Upstream product

• 101039-89-8 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)-5-fluorouracil 
• 76-83-5 trityl chloride 
• 50-91-9 5-Fluoro-2'-deoxyuridine 
• 4031-24-7 1-(2-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-fluorouracil 

Downstream Products

• 103285-11-6 1-(5-O-Trityl-2-deoxy-β-D-lyxofuranosyl)-5-fluorouracil 
• 87190-74-7 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-fluorouracil 
• 101039-90-1 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-fluorouracil 

Relevant articles and documents

Fluorinated pyrimidines. XXIX. Syntheses of 2',3'-dehydro-5-fluoro-2'-deoxyuridine and 2',3'-dideoxy-5-fluorouridine.

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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.