Reactions of Nucleophiles with Reactive Intermediates in the 3,4,6-Tri-O-benzyl-D-glucal-TfOH-n-Bu4NI Reaction System

Idil Kasuto Kelson, Ben Ami Feit

Research output: Contribution to journalArticlepeer-review

Abstract

The unique reactive intermediate formed in the 3,4,6-tri-O-benzyl-D-glucal- TfOH (triflic acid)-n-Bu4NI reaction system (in dichloromethane) reacted with nucleophiles in a regio- and stereoselective manner. These selectivities resulted in hitherto unknown compounds, such as benzyl 4,6-di-O-benzyl-2,3-dideoxy-3-iodo-α-glucopyranoside, which was obtained in the presence of an iodide ion as a nucleophile. The corresponding 2-deoxy α-glycosides were obtained exclusively in the corresponding reaction with hydroxylic nucleophiles.

Original languageEnglish
Pages (from-to)827-841
Number of pages15
JournalJournal of Carbohydrate Chemistry
Volume22
Issue number9
DOIs
StatePublished - 2003

Keywords

  • 2-deoxyglycopyranosides
  • Carbohydrates
  • Glucal
  • Iodosugars
  • Nucleophiles
  • Reactive intermediates

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