FeCl3·6H2O/C: An Efficient and Recyclable Catalyst for the Synthesis of 2,3-Unsaturated O- and S-Glycosides

A novel method for synthesizing 2,3-unsaturated glycosides has been developed using a handy and eco-friendly immobilized catalyst, FeCl 3 ·6H 2 O/C. A series of 2,3-unsaturated O- and S-glycosides were obtained for bioassay from corresponding 3,4,6-tri-O-acetyl-D-glucal and D-galactal in good to exc...

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Bibliographic Details
Published inJournal of carbohydrate chemistry Vol. 33; no. 6; pp. 313 - 325
Main Authors Zhou, Jiafen, Chen, Heshan, Shan, Junjie, Li, Juan, Yang, Guofang, Chen, Xuan, Xin, Kunyun, Zhang, Jianbo, Tang, Jie
Format Journal Article
LanguageEnglish
Published Philadelphia Taylor & Francis 24.07.2014
Taylor & Francis Ltd
Subjects
2,3-Unsaturated glycosides
6H
FeCl
Ferrier-rearrangement
O/C
Recyclable
Tri-O-acetyl-D-glycals
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Summary:A novel method for synthesizing 2,3-unsaturated glycosides has been developed using a handy and eco-friendly immobilized catalyst, FeCl 3 ·6H 2 O/C. A series of 2,3-unsaturated O- and S-glycosides were obtained for bioassay from corresponding 3,4,6-tri-O-acetyl-D-glucal and D-galactal in good to excellent yields (56%-99%) and high anomeric selectivity (α/β = 7:1 to >19:1). Furthermore, the catalyst was efficient on gram-scale reactions and recyclable for at least three times.
ISSN:0732-8303
1532-2327
DOI:10.1080/07328303.2014.941995