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Ulose formation by selenoxide elimination

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
307
Identifiers
DOI: 10.1016/s0008-6215(98)00044-5
Keywords
  • Selenoxide Elimination
  • Enol Formation
  • Epoxide Ring Opening
  • Phenyl Selenide
  • Methyl 2
  • 3-Anhydro-(R)-4
  • 6-O-Benzylidene-α-D-Mannopyranoside

Abstract

Abstract Ring opening of methyl 2,3-anhydro-( R)-4,6- O-benzylidene- α- d-mannopyranoside with phenyl selenide gives ( R)-4,6- O-benzylidene-3- Se-phenyl-3-seleno- α- d-altropyranoside ( 2). Oxidation of ( 2) with H 2O 2 followed by thermolysis gives methyl ( R)-4,6- O-benzylidene-3-deoxy- α- d- erythro-hexopyranosid-2-ulose via syn-elimination and ketoenol tautomerization.

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