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filingDate 1992-05-13-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_29901a951710a2eb68c3a14ee43ed413
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publicationDate 1993-06-29-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber JP-H05163276-A
titleOfInvention Method for inverting the C13 stereochemistry of avermectin aglycone compounds
abstract (57) [Summary] (Modified) [Purpose] To rearrange or epimerize the natural stereochemistry at position 13 of avermectin aglycone, which is usually below the α-direction or molecular plane, to β position. [Structure] An avermectin aglycone compound (formula 2) substituted with a leaving group by acylating a 13α-hydroxy compound (formula 1), and treating the substituted compound with tetraalkylammonium nitrate, the leaving group is substituted, Hydroxy is substituted with a nitrate ester or a nitrooxy group to give 13- Stereochemistry rearranges to β (compound of formula 3). When the nitrooxy group is reduced, it returns to 13-hydroxy group and 13-β- A hydroxy form (compound of formula 4) is obtained. [Effect] This method is simple and has a high yield, and the intermediate 13-nitrooxy compound (formula 3) is itself a powerful antiparasitic agent.
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