ArticleThe Journal of organic chemistry2017
Stereoselective Synthesis of the Equatorial Glycosides of Legionaminic Acid.
Article in The Journal of organic chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 22 citations in OpenAlex.
- Broad-Spectrum Legionaminic Acid-Specific Antibodies in Pooled Human IgGs Revealed by Glycan Microarrays with Chemoenzymatically Synthesized Nonulosonosides.Molecules (Basel, Switzerland) · 2024Article
- Syntheses of Legionaminic Acid, Pseudaminic Acid, Acetaminic Acid, 8-Organic letters · 2022Article
- An efficient and scalable synthesis of 2,4-di-RSC advances · 2021Article
- Influence of substitution at the 5α-Position on the side chain conformation of glucopyranosides.Carbohydrate research · 2021Article
- En Route to the Transformation of Glycoscience: A Chemist's Perspective on Internal and External Crossroads in Glycochemistry.Journal of the American Chemical Society · 2021Article
- Synthesis and Stereocontrolled Equatorially Selective Glycosylation Reactions of a Pseudaminic Acid Donor: Importance of the Side-Chain Conformation and Regioselective Reduction of Azide Protecting Groups.Journal of the American Chemical Society · 2018Article
- A new approach to the synthesis of legionaminic acid analogues.RSC advances · 2018Article
- A Diazido Mannose Analogue as a Chemoenzymatic Synthon for Synthesizing Di-N-acetyllegionaminic Acid-Containing Glycosides.Angewandte Chemie (International ed. in English) · 2018Article
- Oxidative deamination of amino sugars: recent advances.Carbohydrate chemistry · 1979Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The synthesis of a legionaminic acid donor from N-acetylneuraminic acid in 15 steps and 17% overall yield is described. Activation of the adamantanyl thioglycoside in the donor with N-iodosuccinimide and trifluoromethanesulfonic acid in dichloromethane and acetonitrile at -78 °C in the presence of primary, secondary and tertiary alcohols affords the corresponding glycosides in excellent yield and good to excellent equatorial selectivity. In particular, coupling to the 4-OH of a suitably protected neuraminic acid derivative affords a disaccharide that closely resembles the glycosidic linkage in the polylegionaminic acid from the lipopolysaccharide of the Legionella pneumophila virulence factor. A straightforward deprotection sequence enables conversion of the protected glycosides to the free N,N-diacetyllegionaminic acid glycosides.
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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.