Er, Mustafa2022-01-112022-01-112009Er, M. ve Coşkun, N. (2009). "Cis-(-)-menthyl phenylglycidates in the asymmetric synthesis of taxol side chain". Arkivoc, 12, 153-160.1551-7004https://doi.org/10.3998/ark.5550190.0010.c13https://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/ark.5550190.0010.c13http://hdl.handle.net/11452/24008The 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.eninfo:eu-repo/semantics/openAccess3S)-3-phenylisoserineAzidesN-benzoyl-(2RPhenylglycidateTaxol side chainZn-TMSCL reductionZinc-chlorotrimethylsilaneConvenient synthesisReductionAzidesPhenylisoserineSemisynthesisResolutionAnalogsEsterChemistryArticle0002732956000132-s2.0-7795322785415316012Chemistry, organicCytoxazone; Oxazolidinones; Stereochemistry