Journal ArticleDOI
Reaction of 2,3-unsaturated aryl glycosides with lewis acids : a convenient entry to C-aryl glycosides
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TLDR
In this article, a facile synthesis of 2,3-unsaturated aryl glycosides by BF 3.Et 2 O mediated O to C transformation was reported.About:
This article is published in Tetrahedron Letters.The article was published on 1992-05-19. It has received 22 citations till now. The article focuses on the topics: Aryl & Lewis acids and bases.read more
Citations
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Journal ArticleDOI
Total Synthesis of Aryl C-Glycoside Natural Products: Strategies and Tactics
TL;DR: The aryl C-glycoside structure is, among the plenty of biologically active natural products, one of the distinct motifs embedded, and the synthetic strategies and tactics employed in the total synthesis of this class of natural products.
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.
Journal ArticleDOI
The [1, 3] O-to-C rearrangement: opportunities for stereoselective synthesis
TL;DR: This perspective analyzes the various methods used for the activation and [1, 3] rearrangement of vinyl ethers with an emphasis on mechanism and applications to stereoselective synthesis.
Journal ArticleDOI
Aryl and Allyl C-Glycosidation Methods Using Unprotected Sugars
TL;DR: In this paper, aryl and allyl C-glycosidation methods using unprotected sugars as glycosyl donors have been developed, which are versatile synthetic intermediates for the syntheses of optically active natural products.
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 mentioned in this paper.
References
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Journal ArticleDOI
A simple diastereoselective synthesis of 2',3'-unsaturated aryl c-glucopyranosides
Giovanni Casiraghi,Mara Cornia,Gloria Rassu,Lucia Zetta,Giovanna Gasparri Fava,Marisa Ferrari Belicchi +5 more
TL;DR: The regio-and stereoselective arylation at the anomer center of 3,4,6-tri-O -acetyl-D-glucal by means of bromomagnesium phenolates as mentioned in this paper allows direct preparation of 2',3'-unsaturated 1-C -aryl-α-D glycosides.
Journal ArticleDOI
Synthesis of (2-deoxy-α-d-glyc-2-enopyranosyl)arenes by stereospecific counjugate-addition of organocopper reagents to peracetylated hex-1-enopyran-3-uloses
TL;DR: In this paper, the reaction of peracetylated 1,5-anhydro-2-deoxyhex-1-eno-3-uloses with higher-order cyanoorganocuprate in oxolane at low temperature in the presence of acetic anhydride afforded the corresponding glycosylarenes in good yields.