ArticleThe Journal of organic chemistry2018
Stereocontrolled Synthesis of α-Xylofuranosides Using a Conformationally Restricted Donor.
Article in The Journal of organic chemistry, 2018. 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.
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Who cites it
9 citing papers in PubMed, 23 citations in OpenAlex.
- ZnIMolecules (Basel, Switzerland) · 2024Review
- B(CACS omega · 2024Article
- An SCCS chemistry · 2022Article
- Stereoselective 1,2-Journal of the American Chemical Society · 2022Article
- Total Synthesis of a Partial Structure from Arabinogalactan and Its Application for Allergy Prevention.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Lipoarabinomannan as a Point-of-Care Assay for Diagnosis of Tuberculosis: How Far Are We to Use It?Frontiers in microbiology · 2021Review
- Article
- Stereospecific Furanosylations Catalyzed by Bis-thiourea Hydrogen-Bond Donors.Journal of the American Chemical Society · 2020Article
- Furanosyl Oxocarbenium Ion Conformational Energy Landscape Maps as a Tool to Study the Glycosylation Stereoselectivity of 2-Azidofuranoses, 2-Fluorofuranoses and Methyl Furanosyl Uronates.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A number of biologically relevant glycoconjugates possess 1,2- cis-furanosidic linkages, a class of glycosidic bond that remains challenging to introduce with high stereoselectivity. In this paper, we report an approach to one family of such linkages, α-xylofuranosides, via the use of thioglycoside donors possessing a conformationally restricting xylylene protecting group. The method was shown to provide the desired targets in good to excellent yield and stereoselectivity. Computational investigations support the proposal that the protecting group locks the electrophilic intermediate in these reactions into a conformation that leads to the high selectivity. The power of the methodology was demonstrated through the synthesis of a complex hexasaccharide motif from lipoarabinomannan, an immunomodulatory polysaccharide from mycobacteria.
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Registered trials
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