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Synlett 1991; 1991(8): 529-538
DOI: 10.1055/s-1991-20789
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Stereocontrolled Manipulations of Chromatographically Resolved Pyranosides

Eugene A. Mash*
  • *Department of Chemistry, The University of Arizona, Tucson, Arizona 85721, USA
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Publication History

Publication Date:
07 March 2002 (online)

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Diastereoisomeric pyranoside acetals derived from enantiomerically pure α-hydroxy esters are readily separated by simple column chromatography. The "resolved" chirality center at the anomeric carbon can be used as a control element in synthetic manipulations of the pyranoside ring. 1. Introduction 2. Prior Art - Racemic Dihydropyranosides 3. Chromatographic Resolutions of Diastereoisomeric Pyranosides and Furanosides 4. Sterically Controlled Manipulations of Resolved Pyranosides 5. Chelation Controlled Manipulations of Resolved Pyranosides 5.1 Synthesis of (R)-(-)-Mevalonolactone 5.2 Synthesis of a Mevinic Acid Lactone Precursor 5.3 Approaches to the 4-Ethylamino Sugar of Calicheamicin γ1α 1 6. Conclusion

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