Erythrose sesqui-acetals as electrophiles. 2-Deoxy-C-nucleosides from D-glucose.

Robin Polt, Thusitha Wijayarathe

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

Cleavage of glucosides with NalO4 in MeOH furnishes sesqui-acetals (protected dialdehydes). Olefination of these substrates, followed by endocyclic oxymercuration-demercuration furnishes substituted tetrahydrofurans (1,2-dideoxy-1-aryl-D-ribofuranoses). Proper choice of protecting groups can affect the face selectivity of the oxymercuration step to provide only the desired β-C-anomer.

Original languageEnglish (US)
Pages (from-to)4831-4834
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number37
DOIs
StatePublished - Sep 9 1991

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Erythrose sesqui-acetals as electrophiles. 2-Deoxy-C-nucleosides from D-glucose.'. Together they form a unique fingerprint.

  • Cite this