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Synthesis of 6-deoxy-L-idose and L-acovenose from 1,2: 5,6-di-O-isopropylidene-alpha-D-glucofuranose. 2001

S C Hung, and S R Thopate, and R Puranik
Institute of Chemistry, Academia Sinica, Taipei, Taiwan, ROC. schung@chem.sinica.edu.tw

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.

UI MeSH Term Description Entries
D003837 Deoxy Sugars Sugars that in which one or more hydroxyl groups of the pyranose or furanose ring is substituted by hydrogen. Deoxy Sugar,Sugar, Deoxy,Sugars, Deoxy
D005947 Glucose A primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement. Dextrose,Anhydrous Dextrose,D-Glucose,Glucose Monohydrate,Glucose, (DL)-Isomer,Glucose, (alpha-D)-Isomer,Glucose, (beta-D)-Isomer,D Glucose,Dextrose, Anhydrous,Monohydrate, Glucose
D006601 Hexoses MONOSACCHARIDES whose molecules contain six carbon atoms, such as GLUCOSE and FRUCTOSE. They generally have the chemical formula C6H12O6. Hexose
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer

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