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Stereospecific Synthesis of D-Glycero-D-ido-oct-2-ulose

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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary.

 D-Glycero-D-gulo-heptose reacted with 2,2-dimethoxypropane to give its 2,3:6,7-di-O-isopropylidene derivative. Its base-catalyzed addition to formaldehyde resulted in the formation of 2,3:6,7-di-O-isopropylidene-2-C-(hydroxymethyl)-D-glycero-D-gulo-heptofuranose. After acid hydrolysis of this aldolization product, a new branched-chain aldose, 2-C-(hydroxymethyl)-D-glycero-D-gulo-heptose, was obtained, which was stereospecifically rearranged under the catalytic action of molybdic acid to D-glycero-D-ido-oct-2-ulose.

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Authors and Affiliations

  1. Institute of Chemistry, Slovak Academy of Sciences, SK-84238 Bratislava, Slovakia, , , , ,

    Zuzana Hricovíniová, Miloš Hricovíni & Ladislav Petruš

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  1. Zuzana Hricovíniová
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  2. Miloš Hricovíni
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  3. Ladislav Petruš
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Received October 17, 2000. Accepted December 4, 2000

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Hricovíniová, Z., Hricovíni, M. & Petruš, L. Stereospecific Synthesis of D-Glycero-D-ido-oct-2-ulose. Monatshefte fuer Chemie 132, 731–737 (2001). https://doi.org/10.1007/s007060170088

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  • DOI: https://doi.org/10.1007/s007060170088

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