ArticleJournal of the American Chemical Society2012
De novo asymmetric synthesis of all-D-, all-L-, and D-/L-oligosaccharides using atom-less protecting groups.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- De Novo Design and Asymmetric Synthesis of aOrganic letters · 2025Article
- Exploring a De Novo Route to Bradyrhizose: Synthesis and Isomeric Equilibrium of Bradyrhizose DiastereomersChemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Review
- Synthesis of glycoconjugates utilizing the regioselectivity of a lytic polysaccharide monooxygenase.Scientific reports · 2020Article
- Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide.Organic letters · 2020Article
- Versatile Glycosyl Sulfonates in β-Selective C-Glycosylation.Angewandte Chemie (International ed. in English) · 2020Article
- RapidOrganic letters · 2019Article
- Methods for 2-Deoxyglycoside Synthesis.Chemical reviews · 2018Review
- Comprehensive review of chemical strategies for the preparation of new aminoglycosides and their biological activities.Chemical Society reviews · 2018Review
- Palladium-Catalyzed α-Stereoselective O-Glycosylation of O(3)-Acylated Glycals.Organic letters · 2017Article
- Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals.Angewandte Chemie (International ed. in English) · 2017Article
- Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions.Science (New York, N.Y.) · 2017Article
- Synthesis of D-Beilstein journal of organic chemistry · 2017Article
- Article
- Stereoselective synthesis of protected l- and d-dideoxysugars and analoguesChemical science · 2016Article
- Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.RSC advances · 2016Article
- A Survey of Recent Synthetic Applications of 2,3-Dideoxy-Hex-2-enopyranosides.Molecules (Basel, Switzerland) · 2015Review
- Digitoxin analogues with improved anticytomegalovirus activity.ACS medicinal chemistry letters · 2014Article
- Merremoside D: de novo synthesis of the purported structure, NMR analysis, and comparison of spectral data.Organic letters · 2014Article
- De novo asymmetric synthesis of oligo-rhamno di- and tri-saccharides related to the anthrax tetrasaccharide.Tetrahedron · 2013Article
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Authors and funding
5 authors.
Funding
Abstract
Oligosaccharide synthesis is hindered by the need for multiple steps as well as numerous selective protections and deprotections. Herein we report a highly efficient de novo route to various oligosaccharide motifs, of use for biological and medicinal structure activity studies. The key to the overall efficiency is the judicious use of asymmetric catalysis and synthetic design. These green principles include the bidirectional use of highly stereoselective catalysis (Pd(0)-catalyzed glycosylation/post-glycosylation). In addition, the chemoselective use of C-C and C-O π-bond functionality, as atom-less protecting groups as well as an anomeric directing group (via a Pd-π-allyl), highlights the atom-economical aspects of the route to a divergent set of natural and unnatural oligosaccharides (i.e., various d-/l-diastereomers of oligosaccharides as well as deoxysugars which lack C-2 anomeric directing groups). For example, in only 12 steps, the construction of a highly branched heptasaccharide with 35 stereocenters was accomplished from an achiral acylfuran.
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