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Stereoselective Synthesis of Bishomo-inositols as Glycosidase Inhibitors
Date
2009-01-02
Author
Baran, Arif
Balcı, Metin
Metadata
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This work is licensed under a
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
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For the synthesis of various bishomo-inositol derivatives, 1,3,3a,7a-tetrahydro-2-benzofuran was used as the key compound. For further functionalization of the diene unit, the diene was subjected to photooxygenation, epoxidation, and cis-hydroxylation reactions. The endoperoxide linkage was cleaved by thiourea. The remaining double bond was subjected to epoxidation and cis-hydroxylation reactions. The epoxide rings and tetrahydrofuran rings formed were opened by acid-catalyzed reaction with sulfamic acid. The combination of these reactions resulted in the formation of various new inositol derivatives such as bishomo-chiro-inositol, bishomo-myo-inositol, and two isomeric bishomo-allo-inositols.
Subject Keywords
COST-EFFECTIVE CATALYST
,
STEREOSPECIFIC SYNTHESIS
,
FACIAL SELECTIVITY
,
SCYLLO-INOSITOL
,
SULFAMIC ACID
,
MUCO-INOSITOL
,
CONDURITOL-F
,
L-CHIRO
,
TRISPHOSPHATE
,
DERIVATIVES
URI
https://hdl.handle.net/11511/57683
Journal
JOURNAL OF ORGANIC CHEMISTRY
DOI
https://doi.org/10.1021/jo801344f
Collections
Graduate School of Natural and Applied Sciences, Article