The anomeric Pudovik rearrangement

Spencer Knapp, Kehinde Ajayi

Research output: Contribution to journalArticlepeer-review

6 Scopus citations


The O,O-dibenzyl-S-glycosyl phosphothioite derived from 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-thio-α-d-glucopyranose rearranges under the influence of triethylborane and air to provide the corresponding 1-C-pyranosyl-O,O-dibenzylphosphonothioate, a new type of carbohydrate derivative. The isomeric beta phosphothioite is compared, and evidence of a radical chain mechanism for the Pudovik rearrangement is presented.

Original languageEnglish (US)
Pages (from-to)1945-1949
Number of pages5
JournalTetrahedron Letters
Issue number11
StatePublished - Mar 12 2007

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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