Journal
TETRAHEDRON LETTERS
Volume 55, Issue 42, Pages 5813-5816Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.08.092
Keywords
Y(OTf)(3); 3,4,6-Tri-O-acetyl-D-glucal; 3,4,6-Tri-O-benzyl-D-glucal; 3,4-Di-O-acetyl-L-rhamnal; 2,3-Unsaturated glycoside; Ferrier Rearrangement
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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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By using Y(OTf)(3) as the catalyst, a series of 2,3-unsaturated-glucosides have been synthesized from 3,4,6-tri-O-acetyl-D-glucal, 3,4-di-O-acetyl-L-rhamnal, and 3,4,6-tri-O-benzyl-D-glucal under mild reaction conditions in good yields with high anomeric selectivities. It was found that, in this reaction, 3,4,6-tri-O-benzyl-D-glucal behaved differently from the other two glucals when it was reacted with phenol, O-benzyl glucoside instead of O-phenyl glucoside formed as the sole product. An explanation is given for this phenomenon. (C) 2014 Elsevier Ltd. All rights reserved.
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