73189-04-5

Basic information

• Product Name: Thymidine, 3'-O-(triphenylmethyl)-
• CAS NO: 73189-04-5
• Molecular Formula: C29H28N2O5
• Molecular Weight: 484.552
• Mol File: 73189-04-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Thymidine, 3'-O-(triphenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Thymidine, 3'-O-(triphenylmethyl)-(73189-04-5)
• EPA Substance Registry System: Thymidine, 3'-O-(triphenylmethyl)-(73189-04-5)

Safety Data

• Hazardous Substances Data: 73189-04-5(Hazardous Substances Data)

Upstream product

• 73189-05-6 5'-O-isobutoxycarbonyl-3'-O-tritylthymidine 
• 52417-07-9 3′,5′-di-O-trityl-thymidine 
• 76-83-5 trityl chloride 
• 50-89-5 thymidine 
• 25442-44-8 1-(3'-iodo-2',3'-dideoxy-5'-O-trityl-β-D-erythro-pentofuranosyl)thymine 
• 13084-59-8 5'-O-isobutoxycarbonylthymidine 
• 7791-71-1 5'-O-tritylthymidine 
• 35898-29-4 5'-benzoylthymidine 
• 1465077-11-5 C₃₆H₃₂N₂O₆ 
• 17331-53-2 3'-O-benzoylthymidine 

Relevant articles and documents

In search of Flavivirus inhibitors part 2: Tritylated, diphenylmethylated and other alkylated nucleoside analogues

Several flaviviruses, such as the yellow fever virus and the dengue virus cause severe and potentially lethal infection in man. Following up on our initial hit 3′,5′-bistritylated uridine 1, a series of alkylated nucleoside analogues were synthesized and evaluated for their in vitro antiviral activities against dengue fever virus and yellow fever virus. Hereto, alkyl and aryl groups were attached at various positions of the sugar ring combined with subtle variation of the heterocyclic base. Among the new series of derivatives, 3′,5′-di-O-trityl-5-fluoro-2′-deoxyuridine (39) was the most efficient in this series and inhibited both yellow fever virus and dengue virus replication with a 50% effective concentration (EC50) of ～1 μg/mL without considerable cytotoxicity. The other fluorinated derivatives proved more toxic. Almost all diphenylmethylated pyrimidine nucleosides with 3′,5′-di-O-benzhydryl-2′-deoxyuridine (50) as the example were endowed with strong cytotoxic effects down to 1 μg/mL.

Protecting groups transfer: Unusual method of removal of tr and TBDMS groups by transetherification

The triphenylmethyl (Tr) group undergoes a transfer (transetherification or disproportionation) between the molecules of 5'-O-Tr-2'-deoxynucleosides in a process mediated by anhydrous sulfates of Cu+2, Fe+2, or Ni+2 to yield mixtures of 3',5'-bis-O-Tr and 3'-O-Tr products. If phenylmethanol is present in a reaction medium, detritylation results with concomitant formation of phenylmethyl triphenylmethyl ether. The behavior of t-butyldimethylsilyl (TBDMS) group in 5'-O-TBDMS-2'-deoxynucleosides is exactly the same. Such type of transetherifications was not observed before for the O-Tr and O-TBDMS groups. Copyright Taylor & Francis Group, LLC.

Two-Stage Synthesis of 3'-O-Tritylthymidine via Hydrolysis of 3',5'-Di-O-tritylthymidine; Comparison with Alternative Methods

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