2014
DOI: 10.1039/c3ob42491j
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A new approach towards the synthesis of pseudaminic acid analogues

Abstract: The pseudaminic acids are a family of 5,7-diamino-3,5,7,9-tetradeoxynonulosonic acids that are essential components of bacterial polysaccharides and glycoproteins. This paper describes our approach towards the synthesis of analogues of pseudaminic acid, and involves the efficient introduction of the requisite nitrogen functionalities from a readily available precursor.

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Cited by 28 publications
(55 citation statements)
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“…We present improvements to the oxidative deamination of NeuAc employing levulinic acid and trifluoromethanesulfonic acid as nucleophile that considerably shorten the approach to the introduction of the axial azido group compared to the more conventional approach of Kiefel and coworkers. 1819 Finally, we reinvestigate the azide moiety as a protecting group for N5 51 in the formation of NeuAc glycosides and report, contrary to the earlier literature, 5254 that high equatorial selectivity with such donors is not restricted to primary acceptors.…”
Section: Introductionmentioning
confidence: 70%
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“…We present improvements to the oxidative deamination of NeuAc employing levulinic acid and trifluoromethanesulfonic acid as nucleophile that considerably shorten the approach to the introduction of the axial azido group compared to the more conventional approach of Kiefel and coworkers. 1819 Finally, we reinvestigate the azide moiety as a protecting group for N5 51 in the formation of NeuAc glycosides and report, contrary to the earlier literature, 5254 that high equatorial selectivity with such donors is not restricted to primary acceptors.…”
Section: Introductionmentioning
confidence: 70%
“…1819 On the basis of extensive experimentation, we have rationalized the stereoretentive nature of the deamination reaction on the basis of participation by the pyranoside ring oxygen in the displacement of molecular nitrogen, via an oxabicyclo[3.1.0]hexanium ion. 23 This process is facilitated by the extreme leaving group ability of molecular nitrogen to the extent that the ring oxygen intervenes, either directly or at the level of an intermediate carbenium ion, before any intermolecular attack by external nucleophiles including azide.…”
Section: Discussionmentioning
confidence: 99%
“…In 2014, Kiefel and co‐workers reported the synthesis of an analogue of 2 , methyl ester 29 , over 13 steps . Their initial retrosynthetic analysis highlighted sialic acid 2‐keto‐3‐deoxy‐ d ‐glycero‐ d ‐galacto‐nonulosonic acid (KDN) as a potential precursor that would furnish the correct stereochemistry required at C5 and C7 through initial azide inversion.…”
Section: Chemical Approaches To the Synthesis Of Pses And Glycosidesmentioning
confidence: 99%
“… Synthesis of 29 , as reported by Kiefel and co‐workers . TsOH: p ‐toluenesulfonic acid, TFA: trifluoroacetic acid, DIPEA: N , N ‐diisopropylethylamine, TBS: tert ‐butyldimethylsilyl.…”
Section: Chemical Approaches To the Synthesis Of Pses And Glycosidesmentioning
confidence: 99%
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