Journal ArticleDOI
Recent Developments in the Ferrier Rearrangement
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TLDR
A review of recent developments in the use of promoters for the Ferrier rearrangement of O-, N-, C- and S-nucleophiles with glycals can be found in this paper.About:
This article is published in European Journal of Organic Chemistry.The article was published on 2013-11-01. It has received 121 citations till now. The article focuses on the topics: Ferrier rearrangement & Ferrier carbocyclization.read more
Citations
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Journal ArticleDOI
Methods for 2-Deoxyglycoside Synthesis.
Clay S. Bennett,M. Carmen Galan +1 more
TL;DR: This Review covers classical approaches to deoxyglycoside synthesis, as well as more recently developed chemistry that aims to control the selectivity of the reaction through rational design of the promoter.
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Recent progress of C-glycosylation methods in the total synthesis of natural products and pharmaceuticals
TL;DR: This review highlights the C-glycosylation methods that have been practised in the total synthesis of natural products and pharmaceuticals in the past decade.
Journal ArticleDOI
Recent developments in β-C-glycosides: synthesis and applications
Krishnamoorthy Lalitha,Kumarasamy Muthusamy,Y. Siva Prasad,Praveen Kumar Vemula,Subbiah Nagarajan +4 more
TL;DR: In the last few years, considerable progress has been made in the synthesis of C-glycosides as mentioned in this paper, and due to its versatility, C glycosides play a pivotal role in developing novel materials, surfactants and bioactive molecules.
Journal ArticleDOI
Stereoelectronic power of oxygen in control of chemical reactivity: the anomeric effect is not alone
Igor V. Alabugin,Leah Kuhn,Michael G. Medvedev,Michael G. Medvedev,Nikolai V. Krivoshchapov,Nikolai V. Krivoshchapov,Vera A. Vil,Ivan A. Yaremenko,Patricia Mehaffy,Meysam Yarie,Alexander O. Terent'ev,Mohammad Ali Zolfigol +11 more
TL;DR: In this article, the authors evaluate the fundamental connections between the anomeric effect and a broad variety of O-functional groups and highlight the vast implications of AE for the structure and reactivity of organic O-functionalities.
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Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis
TL;DR: This review summarizes the literature on the different transformations of the endo glycals into biologically relevant compounds as well as on the use of glycals as chiral building blocks for the synthesis of various natural products such as aspicilin, reblastatin, diospongins, decytospolides, osmundalactones, paclitaxel, isatisine, d-fagomine, and spliceostatin, reported post 2014.
References
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CF3SO3H–SiO2 as catalyst for Ferrier rearrangement: an efficient procedure for the synthesis of pseudoglycosides
Peiran Chen,Shaoshan Wang +1 more
TL;DR: An efficient method for the conversion of 2,4,6-tri-O -acetyl-d -glucal to 2,3-unsaturated glycosides by using triflic acid on SiO 2 as catalyst has been established.
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Synthesis of cytosinine, the nucleoside component of antibiotic blasticidin S☆
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Reactions of N‐, S‐ and O‐Nucleophiles with 3,4,6‐Tri‐O‐benzyl‐D‐glucal Mediated by Triphenylphosphane Hydrobromide versus Those with HY Zeolite
Amélia P. Rauter,Tânia Santos de Almeida,Ana I. Vicente,Verónica Ribeiro,João C. Bordado,J.P. Marques,Fernando Ramôa Ribeiro,Maria João Ferreira,Conceição Oliveira,Michel Guisnet +9 more
TL;DR: In this article, triphenylphosphane hydrobromide was used as a catalyst for N-N bond formation in dichloromethane or THF, with the first use of HY zeolite to promote theFerrier rearrangement.
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LiBF4-mediated C-glycosylation of glycals with allyltrimethylsilane: a facile synthesis of allyl C-glycosylic compounds☆
TL;DR: The treatment of glycals with allyltrimethylsilane in the presence of lithium tetrafluoroborate in acetonitrile gave the corresponding allyl 2,3-unsaturated C-glycosylic compounds in excellent yields with high anomeric selectivity.
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Reaction of D-glycals with azidotrimethylsilane.
TL;DR: The treatment of 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabino-hex-1-enitol with azidotrimethylsilane by the aid of a catalytic amount of Yb(OTf).
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