Oxidation of glycoside substituted taxanes to taxol or taxol pre

Details Oxidation of glycoside substituted taxanes to taxol or taxol pre Oxidation of glycoside substituted taxanes to taxol or taxol pre

1993-10-07

1995-05-02

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549414, 549510, C07D30514

Patent

active

054121167

ABSTRACT:
A process for the conversion of glycoside substituted taxanes to taxol and related compounds that can serve as precursors to taxol. The process includes the oxidation of glycoside substituted taxanes to convert the glycoside to the hydroxyl group. The oxidation can occur in the presence of an acid or followed by treatment with acid. Application of the process to 7-xylosyl taxol ("XT") yields taxol; application to other glycoside substituted taxanes forms compounds that can serve as precursors for taxol. The process includes the formation of certain new taxol related intermediate compounds having a hemialdal at the C-7 site on the taxane ring, which hemialdal can then be converted to taxol or taxol precursors. Since glycoside substituted taxanes are isolated with taxol from naturally occurring biomass, their conversion to taxol using the process of the present invention significantly improves the total yield of taxol from natural sources.

REFERENCES:
patent: 4924011 (1990-05-01), Denis et al.
patent: 5200534 (1993-04-01), Rao

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