Topic
Ferrier rearrangement
About: Ferrier rearrangement is a research topic. Over the lifetime, 321 publications have been published within this topic receiving 5524 citations.
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TL;DR: By using Hf(OTf)4 as the catalyst, a series of 2,3-N- and C-unsaturated-glucosides have been synthesized from 3,4,6-tri-O-acetyl-d -glucal, 2, 4,6,tri- O-benzyl- d -GLucal and ((2R,3S)-3-acetoxy-2,3,dihydrofuran-2-yl)methyl acetate under mild reaction conditions in good yields with high
5 citations
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TL;DR: In this article, a novel glycal-based O-glycosylation reaction, in which the substrates are not only peracetyl glycals but also perbenzyl glucals to afford the corresponding 2,3-unsaturated-O-glucosides via Ferrier rearrangement, was developed.
Abstract: We have developed a novel glycal-based O-glycosylation reaction, in which the substrates are not only peracetyl glycals but also perbenzyl glucals to afford the corresponding 2,3-unsaturated-O-glycosides via Ferrier rearrangement. The reaction of the perbenzyl glucal with various alcohols catalyzed by ferric sulfate hydrate (Fe2(SO4)3·xH2O) was successfully carried out to give 2,3-unsaturated d-O-glucosides with exclusive α-selectivity and no formation of addition products 2-deoxy hexopyranosides was observed. It is the first report on peralkyl glycal efficiently undergoing Ferrier rearrangement instead of addition of alcohols catalyzed by Lewis acids. Fe2(SO4)3·xH2O is an effective, convenient, and environmentally benign heterogeneous catalyst. It has low catalytic loading and recyclable without significant loss of activity.
5 citations
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TL;DR: The synthesis of a novel carbasugar amino acid (15), starting from D‐glucose and using the Ferrier rearrangement as a key step, is reported.
5 citations
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18 May 2011
TL;DR: In this paper, a method for preparing 4, 6-dibenzyl-2, 3-unsaturated glucoside is described, which is characterized by comprising the following steps of: mixing 3, 4-6-tri-O-benzyl glucal and dichloromethane, acetonitrile, tetrahydrofuran, N, N-dimethylformamide, acetone or diethyl ether in a molar volume ratio of 1 mol: (5-50) L, adding a sulfuric acid/silica
Abstract: The invention discloses a method for preparing 4, 6-dibenzyl-2, 3-unsaturated glucoside, which is characterized by comprising the following steps of: mixing 3, 4, 6-tri-O-benzyl glucal and dichloromethane, acetonitrile, tetrahydrofuran, N, N-dimethylformamide, acetone or diethyl ether in a molar volume ratio of 1 mol: (5-50) L, adding a sulfuric acid/silica catalyst and an oxygen- or sulfur-containing nucleophilic receptor under stirring, undergoing a rearrangement reaction of 3, 4, 6-tri-O-benzyl glucal at a temperature of 0-50 DEG C, filtering out the catalyst after the reaction ends, and concentrating the filter liquor to obtain the 4, 6-dibenzyl-2, 3-unsaturated glucoside. The method for preparing the 4, 6-dibenzyl-2, 3-unsaturated glucoside has the advantages of simple process, convenience in operating, high yield, low production cost and no environmental pollution; the reagent used for synthesis is cheap and easy to get; the dissolvent is cheap and easy to get and has little toxicity; and the method for preparing the 4, 6-dibenzyl-2, 3-unsaturated glucoside is a method for an Ferrier rearrangement reaction of 3, 4, 6-tri-O-benzyl glucose ene with a very good application prospect.
5 citations
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TL;DR: Fluoroboronic acid adsorbed on silica gel (HBF 4 ·SiO 2 ) catalyzes the Ferrier rearrangement of per-O-acetylated glycals with alcohols and sulfonamides to give 2,3-unsaturated O- and N-glycosides in good to excellent yield and with high α-stereoselectivity as discussed by the authors.
Abstract: Fluoroboronic acid adsorbed on silica gel (HBF 4 ·SiO 2 ) catalyzes the Ferrier rearrangement of per-O-acetylated glycals with alcohols and sulfonamides to give 2,3-unsaturated O- and N-glycosides in good to excellent yield and with high α-stereoselectivity.
5 citations