ArticleThe Journal of organic chemistry2014
Glycosyl dithiocarbamates: β-selective couplings without auxiliary groups.
Article in The Journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
9 citing papers in PubMed.
- 2,3,4,6-Tetra-IUCrData · 2025Article
- Complement receptor 3-dependent engagement byOpen biology · 2024Article
- Cooperatively Catalyzed Activation of Thioglycosides That Bypasses Intermediacy of Glycosyl Halides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Interaction Between Dendritic Cells andFrontiers in cellular and infection microbiology · 2020Article
- Matching Glycosyl Donor Reactivity to Sulfonate Leaving Group Ability Permits SJournal of the American Chemical Society · 2019Article
- Stereoselective oxidative glycosylation of anomeric nucleophiles with alcohols and carboxylic acids.Nature communications · 2018Article
- A minimalist approach to stereoselective glycosylation with unprotected donors.Nature communications · 2017Article
- Chemical O-Glycosylations: An Overview.ChemistryOpen · 2016Review
- PRACTICAL SYNTHESIS OF AROMATIC DITHIOCARBAMATES.Synthetic communicationsArticle
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
3 authors.
Funding
Abstract
In this article, we evaluate glycosyl dithiocarbamates (DTCs) with unprotected C2 hydroxyls as donors in β-linked oligosaccharide synthesis. We report a mild, one-pot conversion of glycals into β-glycosyl DTCs via DMDO oxidation with subsequent ring opening by DTC salts, which can be generated in situ from secondary amines and CS2. Glycosyl DTCs are readily activated with Cu(I) or Cu(II) triflate at low temperatures and are amenable to reiterative synthesis strategies, as demonstrated by the efficient construction of a tri-β-1,6-linked tetrasaccharide. Glycosyl DTC couplings are highly β-selective despite the absence of a preexisting C2 auxiliary group. We provide evidence that the directing effect is mediated by the C2 hydroxyl itself via the putative formation of a cis-fused bicyclic intermediate.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.