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cis-(-)-Menthyl phenylglycidates in the asymmetric synthesis of taxol side chain

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dc.creator Er, Mustafa
dc.creator Coskun, Necdet
dc.date 2008-12-31T22:00:00Z
dc.date.accessioned 2020-10-06T09:49:21Z
dc.date.available 2020-10-06T09:49:21Z
dc.identifier 470ced83-d0fc-403c-bf4c-737ab07a8838
dc.identifier 10.3998/ark.5550190.0010.c13
dc.identifier https://avesis.sdu.edu.tr/publication/details/470ced83-d0fc-403c-bf4c-737ab07a8838/oai
dc.identifier.uri http://acikerisim.sdu.edu.tr/xmlui/handle/123456789/58983
dc.description The one-pot azidation and benzoylation of a mixture of cis (-)-menthyl phenylglycidates provide quantitatively the corresponding (2R,3S)-, and (2S,3R)-3-azido-1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)-1-oxo-3-phenylpropan-2-yl benzoate. Enantiopure (2R,3S)-3-azido-1((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)-1-oxo-3-phenylpropan-2-yl benzoate crystallize from MeOH at room temperature in high yields. The reduction of the latter with Zn-TMSCl produces (-)-menthyl 3-benzamido-3-phenyl-2-(trimethylsilyloxy) propanoate which upon simultanious desilylation and hydrolysis provide the taxol side chain N-benzoyl-(2R, 3S)-3-phenylisoserine.
dc.language eng
dc.rights info:eu-repo/semantics/closedAccess
dc.title cis-(-)-Menthyl phenylglycidates in the asymmetric synthesis of taxol side chain
dc.type info:eu-repo/semantics/article


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