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Stereoselektive epoxidierung von di-[3-O-(1,2:5,6-diisopropyliden)-α-D- und α-L-glucofuranosyl]-3,6-hexanooxepin-4,5-dicarboxylat

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
49
Issue
21
Identifiers
DOI: 10.1016/s0040-4020(01)81287-4
Keywords
  • Epoxidation
  • Absolute Configuration
  • Crystal Structure Analysis
  • Photochemistry
Disciplines
  • Chemistry

Abstract

Abstract Epoxidation of the oxepine diester (−)- 1a leads to the oxirane (+)- 2a with ( S, S) configuration in high yield. (+)- 1b on the other hand gives the (1a R,6 R)-oxirane (−)- 2b. (+)- 2a undergoes photochemical ring closure to give (+)-( S, S, S, S)- 3a in 90% yield.

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