Journal ArticleDOI
Selective formation of C-2 azidodeoxy-d-glucose derivatives from d-glucal precursors using the azidonitration reaction
TLDR
The findings allow the azidonitration reaction to be now used for the preparation of a variety of glucosamine building blocks from differentially protected glucal precursors.About:
This article is published in Carbohydrate Research.The article was published on 2000-08-16. It has received 38 citations till now. The article focuses on the topics: Glucal & Acetal.read more
Citations
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Journal ArticleDOI
Recent trends in the synthesis of O-glycosides of 2-amino-2-deoxysugars.
TL;DR: The discovery of new methods for stereoselective glycoside synthesis and convergent oligosaccharide assembly has been critical for the area of glycosciences and the current standing in the field is evaluated.
Journal ArticleDOI
Recent Advances in Transition Metal-Catalyzed Glycosylation
Matthew J. McKay,Hien M. Nguyen +1 more
TL;DR: Recent advancement is highlighted by examining strategies that employ transition metal catalysis in the synthesis of oligosaccharides and glycoconjugates, which are mild and effective for constructing glycosidic bonds with reduced levels of waste through utilization of sub-stoichiometric amounts of transition metals.
Journal ArticleDOI
Nickel-catalyzed stereoselective glycosylation with C(2)-N-substituted benzylidene D-glucosamine and galactosamine trichloroacetimidates for the formation of 1,2-cis-2-amino glycosides. Applications to the synthesis of heparin disaccharides, GPI anchor pseudodisaccharides, and α-GalNAc.
TL;DR: A novel method for the synthesis of 1,2-cis-2-amino glycosides via nickel-catalyzed α-selective glycosylation with C(2)-N-substituted benzylidene D-glucosamine and galactosamine trichloroacetimidates is developed.
Journal ArticleDOI
New Strategies for the Synthesis of Aliphatic Azides.
TL;DR: A review of modern synthetic strategies to access aliphatic azides that have emerged since 2010 is presented in this article, where the challenges and potential opportunities of the topic are outlined.
Journal ArticleDOI
Radical-mediated synthesis of alpha-C-glycosides based on N-acyl galactosamine.
TL;DR: Using anomeric selenides, radical generation and trapping is carried out under conditions that avoid competitive reduction, and this chemistry has been applied to the synthesis of the novel C-glycoside analogue of O-benzyl alpha-D-GalNAc.
References
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Journal ArticleDOI
Biological roles of oligosaccharides: all of the theories are correct
TL;DR: The only common features of the varied functions of oligosaccharides are that they either mediate ‘specific recognition’ events or that they provide ‘modulation’ of biological processes.
Journal ArticleDOI
The azidonitration of tri-O-acetyl-D-galactal
R. U. Lemieux,R. M. Ratcliffe +1 more
TL;DR: In this article, a reaction of 3,4,6,tri-O-acetyl-D-galactal with excess ammonium nitrate and sodium azide in acetonitrile produced 2-azido-1-nitrate addition products (53% β-Galacto, 22% α-GalACTo, and 8% α -Ta...
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Convenient Synthesis of 2‐Azido‐2‐deoxy‐aldoses by Diazo Transfer
TL;DR: Diazo transfer from trifluoromethanesulfonyl azide (TfN3) to 2-amino-2-deoxy-glycoses constitutes a high-yielding, simple procedure for the preparation of partially protected or unprotected 2-azido- 2- deoxy-aldoses.
Journal ArticleDOI
Glycosylimidate, 16. Synthese des Trisaccharids aus der „Repeating Unit”︁ des Kapselpolysaccharids von Neisseria meningitidis (Serogruppe L)
Willy Kinzy,Richard R. Schmidt +1 more
TL;DR: In this article, the trisaccharide β-D-GlcNAc was transformed into the per-O-acetylated trisACcharide α-trichloroacetimidate by removing the 1-Osilyl protective group, reduction of the azido groups, hydrogenolytic debenzylation, and peracetylation.
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Preparation of pyranoid glycal derivatives from phenyl thioglycosides and glycosyl phenyl sulphones
TL;DR: In this article, a pyranoid glycal derivatives with acid-labile protecting groups (acetal, ether, ester) were obtained in excellent yields, and a β-linked 2′-deoxydisaccharide glycal derivative was also prepared from the corresponding disaccharides phenyl thioglycoside.