Short synthesis of octosyl nucleosides

Spencer Knapp, Vinay V. Thakur, Machender R. Madduru, Krishnan Malolanarasimhan, Gregori J. Morriello, George A. Doss

Research output: Contribution to journalArticle

14 Scopus citations

Abstract

Commercial 1,2:5,6-di-O-isopropylidene-α-D-allofuranose was converted to a protected bicyclic octosyl acid thioglycoside donor by a 10-step sequence that features an intramolecular ester enolate alkylation. Glycosylation of N-benzoyladenine and methyl uridine-5-carboxylate followed by deprotection gave the respective nucleosides "octosyl adenine" and octosyl acid A.

Original languageEnglish (US)
Pages (from-to)1335-1337
Number of pages3
JournalOrganic letters
Volume8
Issue number7
DOIs
StatePublished - Mar 30 2006

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Knapp, S., Thakur, V. V., Madduru, M. R., Malolanarasimhan, K., Morriello, G. J., & Doss, G. A. (2006). Short synthesis of octosyl nucleosides. Organic letters, 8(7), 1335-1337. https://doi.org/10.1021/ol0600382