Synthesis of 6-deoxy-L-idose and L-acovenose from 1,2: 5,6-di-O-isopropylidene-alpha-D-glucofuranose.
A practical route toward the synthesis of 6-deoxy-L-idose and L-acovenose from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose is described. Key steps include the stereoselective hydrogenation of 6-deoxy-1,2:3,5-di-O-isopropylidene-alpha-D-xylo-hex-5-enofuranose, regioselective protection of 6-deoxy-1,2-O-isopropylidene-beta-L-idofuranose at 0-5, and epimerisation of 6-deoxy-5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-beta-L-idofuranose at C-3.
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Institute of Chemistry, Academia Sinica, Taipei, Taiwan, ROC. schung@chem.sinica.edu.tw
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Puranik
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D003837:Deoxy Sugars / Q000138:chemical synthesis*; D005947:Glucose / Q000031:analogs & derivatives / Q000737:chemistry*; D006601:Hexoses / Q000138:chemical synthesis*; D013237:Stereoisomerism
C438083:6-deoxy-idose; D003837:Deoxy Sugars; D006601:Hexoses; C438084:acovenose; C036124:1,2-5,6-di-O-isopropylidene-D-glucofuranose; C011754:6-deoxytalose; D005947:Glucose