Journal ArticleDOI
Microwave-induced, Montmorillonite K10-catalyzed Ferrier rearrangement of tri-O-acetyl-d-galactal: mild, eco-friendly, rapid glycosidation with allylic rearrangement
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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
Montmorillonite K-10 as a mild acid for the Nicholas reaction
TL;DR: The use of Montmorillonite K-10 as a convenient acid component in the Nicholas reaction is described in this paper, which permits functional selectivity, inter-and intramolecular reactions and convenience in the experimental conditions.
Journal ArticleDOI
Reconsidering glycosylations at high temperature: precise microwave heating.
TL;DR: Fast, high-temperature glycosylations using precise microwave heating in the synthesis of oligosaccharides, with both DISAL and widely used trichloroacetimidate glycosy donors in the absence of strong Lewis acids are described.
Journal ArticleDOI
Microwave-assisted, tin-mediated, regioselective 3-O-alkylation of galactosides
TL;DR: In this paper, a microwave-assisted dibutylstannylene-mediated 3-O-alkylation method for galactosides was established, where the alkylation reaction was significantly enhanced by microwave irradiation and allowed the use of an alkylating agent too unstable for incorporation using conventional heating.
Journal ArticleDOI
Indium trichloride promoted stereoselective synthesis of O-glycosides from trialkyl orthoformates
TL;DR: In this paper, a highly stereoselective method for O-glycosylation of glycals and glycosylbromides was developed using orthoformates as acceptors in the presence of InCl 3 to afford the corresponding O -glycopyranosides in 66-94% yield.
Journal ArticleDOI
FeCl3·6H2O/C: An Efficient and Recyclable Catalyst for the Synthesis of 2,3-Unsaturated O- and S-Glycosides
Jiafen Zhou,Heshan Chen,Junjie Shan,Juan Li,Guofang Yang,Xuan Chen,Kunyun Xin,Jianbo Zhang,Jie Tang +8 more
TL;DR: In this paper, a novel method for synthesizing 2,3-unsaturated glycosides using a handy and eco-friendly immobilized catalyst, FeCl3·6H2O/C.
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