Syntheses of D-chiro-3-inosose and (+)-D-chiro inositol

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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C07D31770

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055632815

ABSTRACT:
There are described novel biocatalytic and chemical processes for the synthesis of various oxygenated compounds. Particularly, there are described processes for the synthesis of a useful synthon 12 made by reacting a protected diol (acetonide) with permaganate under appropriate conditions. Such synthon is useful of the synthesis of various pharmaceutically important compounds such as D-chiro-inositol and D-chiro-3-inosose. Also, there are disclosed novel compounds, including specifically the synthon 12 and compounds derived therefrom.

REFERENCES:
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Hudlicky, T.; Price J. D.; Tsunoda, T.--"Efficient and Enantiodivergent Synthesis of (+)- and (-)-Pinitol"; J. Am. Chem. Soc. 1990, 112, 9439-9440.
Rudloff, E. von--"Permanganate Oxidation of Occidentalol: Unexpected Epoxide Formation"; Tetrahedron Letters No. 10, pp. 993-998, 1966, Pergamon Press Ltd., U.K.
Ganey, M. V.; Padykula, R. E.; Berchtold, G. A.; --"Resolution of trans-1,2-Dihydroxy-1,2-dihydrobenzene for the Preparation of Optically Pure Benzene Diol Epoxides. Preparation of Bromo- and Chlorobenzene Diol Epoxides"; J. Org. Chem. 1989, 54, 2787-2793.
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