Modified synthesis of 3′-OTBDPS-protected furanoid glycal

Kartik Temburnikar, Zhibo Zhang, Katherine Seley-Radtke

Research output: Contribution to journalArticlepeer-review

Abstract

Thermolytic cleavage of 3′-OH protected thymidine is the most common method of preparing furanoid glycals. We have observed that glycosidic bond cleavage is more facile when the 5-OH of thymidine was also protected with a silyl group. Addition of trimethylsilyl chloride facilitated cleavage of the glycosidic bond; thus, both modifications are required for the formation of the furanoid glycal. Investigations into the selective deprotection of 5′-silyl versus 3′-silyl and subsequent glycosidic bond cleavage are reported herein.

Original languageEnglish (US)
Pages (from-to)319-327
Number of pages9
JournalNucleosides, Nucleotides and Nucleic Acids
Volume31
Issue number4
DOIs
StatePublished - Apr 1 2012
Externally publishedYes

Keywords

  • C-nucleosides
  • Furanoid glycal

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Genetics

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