Transformation of C4-Methyl Derivatives of Levoglucosenone to 2,5-Dihydrofurans. An Unexpected Intramolecular Oxacyclization

The acid-catalyzed reaction of C 4 -methyl derivatives of levoglucosenone with ethanethiol and propane-1,3-dithiol was studied. The reaction takes a nontrivial route and involves intramolecular oxacyclization to form 2,5-dihydrofurans containing a thioacetal group at C 5 in the side chain. The trans...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2019, Vol.55 (11), p.1661-1668
Main Authors: Davydova, A. N., Sharipov, B. T., Valeev, F. A.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Derivatives
Organic Chemistry
Transformations
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Summary:The acid-catalyzed reaction of C 4 -methyl derivatives of levoglucosenone with ethanethiol and propane-1,3-dithiol was studied. The reaction takes a nontrivial route and involves intramolecular oxacyclization to form 2,5-dihydrofurans containing a thioacetal group at C 5 in the side chain. The transformation provides a short way to synthesize chiral 2,5,5-trialkyl-substituted 2,5-dihydrofurans from levoglucosenone.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428019110034