Addition of trialkylaluminum reagents to glyconolactones. Synthesis of 1-C-methyl GlcNAc oxazoline and thiazoline

Spencer Knapp, Chunhua Yang, Thomas Haimowitz

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

Addition of carbon nucleophiles to 2-acetamido-2-deoxygluconolactones fails for many reagents, but trialkylaluminums add alkyl smoothly. The product of methyl addition to 2-acetamido-2-deoxy-D-gluconolactone has been converted to 1-C-methyl GlcNAc thiazoline, a potential N-acetylhexosaminidase inhibitor, and to an O-protected 1-C-Me GlcNAc oxazoline, a potential 1-C-Me GlcNAc donor.

Original languageEnglish (US)
Pages (from-to)7101-7104
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number39
DOIs
StatePublished - Sep 23 2002

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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