ArticleThe Journal of organic chemistry2012
Stereoselective C-glycoside formation with 2-O-benzyl-4,6-O-benzylidene protected 3-deoxy gluco- and mannopyranoside donors: comparison with O-glycoside formation.
Article in The Journal of organic chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 30 citations in OpenAlex.
- Anomeric Triflates versus Dioxanium Ions: Different Product-Forming Intermediates from 3-Acyl Benzylidene Mannosyl and Glucosyl Donors.The Journal of organic chemistry · 2024Article
- Exploratory N-Protecting Group Manipulation for the Total Synthesis of Zwitterionic Shigella sonnei Oligosaccharides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Synthesis of 3-Deoxy-d-The Journal of organic chemistry · 2020Article
- Mild Cu(OTf)The Journal of organic chemistry · 2020Article
- Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea.Journal of the American Chemical Society · 2020Article
- Defining the SACS central science · 2019Article
- The Experimental Evidence in Support of Glycosylation Mechanisms at the SChemical reviews · 2018Review
- Trifluoromethanesulfonate Anion as Nucleophile in Organic Chemistry.The Journal of organic chemistry · 2017Article
- The influence of acceptor nucleophilicity on the glycosylation reaction mechanism.Chemical science · 2017Article
- Mechanistic Investigations into the Application of Sulfoxides in Carbohydrate Synthesis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Review
- A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art.Carbohydrate research · 2015Review
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Unlike alcohols, the reaction of C-nucleophiles with 2-O-benzyl-4,6-O-benzylidene-protected 3-deoxy-gluco- and mannopyranosyl thioglycosides is highly stereoselective providing the α-C-glycosides in the gluco-series and the β-C-glycosides in the manno-series. Conformational analysis of nucleophilic attack of putative intermediate glycosyl oxocarbenium ions suggests that the observed selectivities for C-glycoside formation can be explained by preferential attack on the opposite face of the oxocarbenium to the C2-H2 bond and that eclipsing interactions with this bond are the main stereodetermining factor. It is argued that the steric interactions in the attack of alcohols (sp(3)-hybridized O) and of typical carbon-based nucleophiles (sp(2) C) on oxocarbenium ions are very different, with the former being less severe, and thus that there is no a priori reason to expect O- and C-glycosylation to exhibit parallel stereoselectivities for attack on a given oxocarbenium ion.
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