Journal ArticleDOI
Microwave-induced, Montmorillonite K10-catalyzed Ferrier rearrangement of tri-O-acetyl-d-galactal: mild, eco-friendly, rapid glycosidation with allylic rearrangement
TLDR
Montmorillonite K10 was found to catalyze, under microwave irradiation, rapid O-glycosidation of 3,4,6-tri-O-acetyl-d-galactal to afford exclusively the alkyl and aryl 2,3-dideoxy-dthreo-hex-2-enopyranosides with very high α-selectivity as mentioned in this paper.About:
This article is published in Tetrahedron Letters.The article was published on 2002-09-16. It has received 46 citations till now. The article focuses on the topics: Ferrier rearrangement & Ferrier carbocyclization.read more
Citations
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Journal ArticleDOI
IBr-CATALYZED O-GLYCOSYLATION OF D-GLUCALS : FACILE SYNTHESIS OF 2,3-UNSATURATED-O-GLYCOSIDES
Dissertation
Chemical approaches toward preparation of water-soluble curcumin derivatives
TL;DR: Development of alternative, efficient and stereo-specific methods for obtaining specific derivatives of curcumin, their characterization, analysis and study of their bioactive attributes and the in vitro antioxidant, antibacterial and antimutagenic properties are presented.
Journal ArticleDOI
Palladium(0)-catalysed synthesis of 2,3- and 3,4-unsaturated aryl β-O-glycosides.
TL;DR: Arylation of 6-O-tert-butyldiphenylsilyl-3,4-di- O-isobutyloxycarbonyl-d-glucal with various phenols in the presence of a catalytic amount of palladium gave the corresponding 2,3- and 3, 4-unsaturated β-O -glycosides.
Journal ArticleDOI
Catalysis and deactivation of montmorillonite K10 in the aryl O -glycosylation of glycosyl trichloroacetoimidates
TL;DR: In this article, the catalysis of montmorillonite K10 for aryl O-glycosylation of glycosyl trichloroacetimidates was investigated.
Journal ArticleDOI
Acid Catalyzed Stereocontrolled Ferrier-Type Glycosylation Assisted by Perfluorinated Solvent
Zhiqiang Liu,Yanzhi Li,Shao-Hua Xiang,Mengke Zuo,Ya Ping Sun,Xingxing Jiang,Rongkai Jiao,Yinghong Wang,Yuqin Fu +8 more
TL;DR: The first application of perfluorinated solvent in the stereoselective formation of O-/S-glycosidic linkages that occurs via a Ferrier rearrangement of acetylated glycals is described.
References
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Journal ArticleDOI
Recent progress in O-glycosylation methods and its application to natural products synthesis
Kazunobu Toshima,Kuniaki Tatsuta +1 more
Book
The anomeric effect
Eusebio Juaristi,Gabriel Cuevas +1 more
TL;DR: This chapter discusses the history and applications of the Anomeric Effect in Organic Synthesis, and some of the applications can be found in the literature on endoelectronic effects of the anomeric effect.
Journal ArticleDOI
Unsaturated carbohydrates. Part IX. Synthesis of 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides from tri-O-acetyl-D-glucal
R. J. Ferrier,N. Prasad +1 more
TL;DR: Tri-O-acetyl-D-glucal undergoes complete reaction with alcohols in benzene solution in the presence of boron trifluoride to give 4,6-di-OðOðAðEðDÞÞ −2,3-dideoxy-α-DÒÞ−EðE Þ−hex-hex-2-enopyranosyl as discussed by the authors, which can be used to prepare the known crystalline ethyl αglucoside easily and in greatly improved
Book ChapterDOI
Substitution-with-Allylic-Rearrangement Reactions of Glycal Derivatives
TL;DR: Glycals (or usually their O-substituted derivatives) are readily converted into 2,3-unsaturated glycosyl compounds with O-, C-, N-, S- or otherwise linked substituents at the anomeric position as discussed by the authors.
Related Papers (5)
Indium trichloride catalyzed glycosidation. An expeditious synthesis of 2,3-unsaturated glycopyranosides†
Protic acid (HClO4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals.
Stereoselective palladium-catalyzed O-glycosylation using glycals
Hahn Kim,Hongbin Men,Chulbom Lee +2 more