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AbstractAbstract
[en] We synthesized D-erythro-sphingosine from D-ribo-phytosphingosine whose process is applicable in large scale. Also developed were the intermediates with orthogonally protected amine at C2 and hydroxides at C1 and C3. Understanding the role of sphingolipids metabolism in the transduction of the extracellular signals gives an opportunity to develop many novel biologically active molecules including anticancer, anti-immflamatory and immunosuppressant agents. All of sphingolipids consists of sphingoid backbone and the diverse pendants on hydroxides and/or amine groups including fatty acids, sugars, phosphate etc. The most important sphingoid backbone occurring all mammalian cells is D-erythro-sphingosine [[(2S,3R,4E)-2-amino-3-hy-droxyoctadec-4-ene-1-ol]. Ample examples of synthetic methods toward D-erythro-sphingosine were reported, most of which required several steps to introduce 2-amino-1,3,-dihydroxy moieties with right configurations.3 D-ribo-phytosphingosine [(2S,3S,4R)-2-amino-1,3,4-octadecanetriol] available in large quantity from fermentation, possesses all eighteen carbons and 2-amino-1,3-diols for D-erythrosphingosine with one extra-hydroxyl group at C4. Thereby, dehydrative removal of one extra-hydroxide at C4 along with one hydrogen at C5 in stereoselective manner may afford D-erythro-sphingosine. Though a few methods were already available for the preparation of D-erythro-sphingosine form D-ribo-phytosphingosine, a more reliable large scale and cheap synthetic route is still needed
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10 refs, 2 figs
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Journal Article
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Bulletin of the Korean Chemical Society; ISSN 0253-2964;
; v. 30(3); p. 535-536

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