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Preparation of methyl 2,3-di-O-mesyl-4,6-thioanhydro-α-d-galactopyranoside and methyl 2-O-mesyl-4,6-thioanhydro-α-d-gulopyranoside

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
325
Issue
4
Identifiers
DOI: 10.1016/s0008-6215(00)00009-4
Keywords
  • Mitsunobu Reaction
  • Thiosugars
  • 2-Oxa-7-Thiabicyclo[4.2.0]Octanes
  • X-Ray Diffraction Analysis
  • 1C4-α-D-Gulopyranose Derivative

Abstract

Abstract Two 2-oxa-7-thiabicyclo[4.2.0]octane derivatives, 4 and 10, with the d- galacto and d- gulo configuration, respectively, were obtained from methyl α- d-glucopyranoside. The thietane cyclization involved a thio-Mitsunobu reaction resulting in a 6-thioacetate, which underwent selective base-catalyzed intramolecular nucleophilic substitution at a C-4 mesylate. The structureS of 4 and 10 were elucidated by X-ray diffraction analysis.

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