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Synthesis of 2-Keto-d- and l-gluconic Acid via Stereoselective Direct Aldol Reactions

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Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Krakow, Poland
Cite this: J. Org. Chem. 2016, 81, 14, 6112–6117
Publication Date (Web):June 29, 2016
https://doi.org/10.1021/acs.joc.6b01068
Copyright © 2016 American Chemical Society
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Abstract

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Stereoselective direct aldol reaction between optically pure d- or l-glyceraldehyde and hydroxyacetylfuran is demonstrated as an efficient and straightforward methodology for the synthesis of six-carbon atom d- and l-arabino-hex-2-ulosonic acids. syn-Selective aldol reactions realized by using either tertiary amines or a dizinc aldol catalyst constitute two parallel routes to the de novo synthesis of orthogonally protected biologically relevant 2-keto-d- and l-gluconic acids.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.6b01068.

  • 1H and 13C NMR for all compounds (PDF)

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Cited By

This article is cited by 5 publications.

  1. Yuli Sun, Chengrong Lu, Bei Zhao, Mingqiang Xue. Enantioselective Hydroboration of Ketones Catalyzed by Rare-Earth Metal Complexes Containing Trost Ligands. The Journal of Organic Chemistry 2020, 85 (16) , 10504-10513. https://doi.org/10.1021/acs.joc.0c00877
  2. Zhiliang Hou, Lei Sun, Daming Wang, Wenjing Sun, Fengjie Cui, Silian Yu. Production of 2-keto-gluconic acid from glucose by immobilized Pseudomonas plecoglossicida resting cells. 3 Biotech 2020, 10 (6) https://doi.org/10.1007/s13205-020-02243-z
  3. Juan Manuel Romo, Pedro Romea, Fèlix Urpí. Direct anti Glycolate Aldol Reaction of Protected Chiral N -Hydroxyacetyl Thiazolidinethiones with Acetals Catalyzed by a Nickel(II) Complex. European Journal of Organic Chemistry 2019, 2019 (36) , 6296-6305. https://doi.org/10.1002/ejoc.201901097
  4. Virginia V. Triantakonstanti, Olga G. Mountanea, Kyriaki-Eleni C. Papoulidou, Thanos Andreou, Theocharis V. Koftis, John K. Gallos. Studies towards the synthesis of ertugliflozin from l-Arabinose. Tetrahedron 2018, 74 (39) , 5700-5708. https://doi.org/10.1016/j.tet.2018.08.005
  5. Sebastian Baś, Rafał Kusy, Monika Pasternak-Suder, Cyril Nicolas, Jacek Mlynarski, Olivier R. Martin. Total synthesis of pipecolic acid and 1- C -alkyl 1,5-iminopentitol derivatives by way of stereoselective aldol reactions from ( S )-isoserinal. Organic & Biomolecular Chemistry 2018, 16 (7) , 1118-1125. https://doi.org/10.1039/C7OB02797D

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