Stereocontrolled manipulations of chromatographically resolved pyranosides

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Abstract

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 γ 1 6. Conclusion.

Original languageEnglish (US)
Pages (from-to)529-538
Number of pages10
JournalSynlett
Volume1991
Issue number8
DOIs
StatePublished - Aug 1 1991

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Acetals
Column chromatography
Chirality
Lactones
Chelation
Sugars
Esters
Carbon
Acids
mevalonolactone

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Stereocontrolled manipulations of chromatographically resolved pyranosides. / Mash, Eugene A.

In: Synlett, Vol. 1991, No. 8, 01.08.1991, p. 529-538.

Research output: Contribution to journalArticle

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