Reaction of N3-benzoyl-3′,5′-O-(di-tertbutylsilanediyl)uridine with hindered electrophiles: Intermolecular N3 to 2′-O protecting group transfer

Lei Zhu, Osvaldo Dos Santos, Nadrian C. Seeman, James W. Canary

Research output: Contribution to journalArticlepeer-review


The compound N3-benzoyl-3′,5′-O-(di-tert-butylsilanediyl)uridine 2 was alkylated with various alkyl iodides in CH3CN in the presence of base. Normal 2′-O-alkylated products were obtained with methyl or benzyl iodide. If hindered alkyl iodides with β-branching such as 2-ethylbutyl iodide were used as electrophiles under the same conditions, N3-alkyl-2′-O-benzoyl uridine derivatives were produced. This unexpected transformation is usually dormant with reactive alkylating agents, but expressed with sterically hindered, less reactive electrophiles. This unwanted reaction gives isomeric products whose spectra differ in only subtle ways from target compounds.

Original languageEnglish (US)
Pages (from-to)723-735
Number of pages13
JournalNucleosides, Nucleotides and Nucleic Acids
Issue number10
StatePublished - 2002


  • 2′-O-Alkyl ribonucleosides
  • Alkylation reaction
  • Protecting group

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Genetics


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