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
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Journal ArticleDOI
Microwave‐Induced, Montmorillonite K10‐Catalyzed Ferrier Rearrangement of tri‐O‐Acetyl‐D‐galactal: Mild, Eco‐Friendly, Rapid Glycosidation with Allylic Rearrangement.
TL;DR: 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 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.
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Hahn Kim,Hongbin Men,Chulbom Lee +2 more