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
Current perspectives on microwave-enhanced reactions of monosaccharides promoted by heterogeneous catalysts
TL;DR: In this article, the use of ion exchange resins, zeolites, clays and metal oxides as convenient mediators for key transformations of carbohydrates is discussed, and a special emphasis is placed on use of (doped) mineral supports, in solventless conditions, as clean promoters in combination with microwave dielectric heating.
Journal ArticleDOI
NaHSO(4) supported on silica gel: an alternative catalyst for Ferrier rearrangement of glycals.
TL;DR: NaHSO(4) supported on silica gel catalyses the Ferrier rearrangement reaction of 3,4,6-tri-O-acetyl-D-glucal with alcohols and thiols to give the corresponding 2,3-unsaturated glycosides in high anomeric selectivity and good to excellent yield in short reaction time.
Journal ArticleDOI
Effective and chemoselective glycosylations using 2,3-unsaturated sugars
Shunichi Kusumi,Kaname Sasaki,Sainan Wang,Tatsuya Watanabe,Daisuke Takahashi,Kazunobu Toshima +5 more
TL;DR: The highly reactive 2,3-unsaturated glycosyl acetates were found to be useful in the synthesis of the O-glycosides of low reactive tertiary alcohols and effectively realized via combinatorial techniques in short-steps using three types of Glycosyl donors to construct several types of deoxyoligosaccharides.
Journal ArticleDOI
Semi-Synthesis of new glycosidic triazole derivatives of dihydrocucurbitacin B
Ana Luísa Malaco Morotti,Karen L. Lang,Ivone Carvalho,Eloir Paulo Schenkel,Lílian Sibelle Campos Bernardes +4 more
TL;DR: In this paper, the synthesis of a 2β-O -galactoside of dihydrocucurbitacin B and eight new glycosides containing triazole moiety between the cucurbitane skeleton and the monosaccharidic unit was reported.
Journal ArticleDOI
Microwave‐Enhanced Ferrier Reaction: A Facile Synthesis of 2,3‐Unsaturated‐O‐Glycosides Under Solvent‐Free Conditions
Wenting Du,Yong‐Zhou Hu +1 more
TL;DR: A variety of 2,3-unsaturated O-glycosides have been prepared by the Ferrier rearrangement of acetyl protected glycals under microwave irradiation using silica gel as an acid catalyst as discussed by the authors.
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