Journal
TETRAHEDRON
Volume 69, Issue 23, Pages 4524-4531Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.04.051
Keywords
Type I Ferrier rearrangement; TiCl3(OTF); Tri-O-acetyl-D-glucal; 2,3-Unsaturated-O-glycoside; 3,4,6-Tri-O-acetyl-D-glucal
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Funding
- National Natural Science Foundation of China (NSFC) [21272305]
- Natural Science Foundation of Shanghai Municipality [12ZR1400200]
- Fundamental Research Funds for the Central Universities
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An efficient type I Ferrier rearrangement reaction system for the synthesis of 2,3-unsaturated-O-glycosides has been established by using TiCl3(OTf) as the catalyst. A series of 2,3-unsaturated-O-glucosides were prepared from 3,4,6-tri-O-acetyl-D-glucal in good yield and high anomeric selectivity. (C) 2013 Elsevier Ltd. All rights reserved.
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