117486-34-7Relevant academic research and scientific papers
Regio- and stereoselective methods for the conversion of (2S,3R)-β-phenylglycidic acid esters to taxoids and other enantiopure (2R,3S)-phenylisoserine esters
Afon'Kin,Kostrikin,Shumeiko,Popov,Matveev,Matvienko,Zabudkin
, p. 2149 - 2162 (2013/10/01)
A novel efficient method was proposed for the synthesis of enantiopure precursors of taxane-containing cytostatics, i.e., methyl esters of (2R,3S)- and (2S,3R)-N-benzoylphenylisoserine and similar taxoid esters. The method is based on the regio- and stereoselective hydrobromolysis of the corresponding trans-β-phenyl glycidate enatiomers, consecutive reactions of O-acylcarbamoylation of the obtained 3-bromohydrins, intramolecular cyclization to 4-phenyloxazolidin-2-one-5-carboxylic acid derivatives, and oxazolidinone ring opening.
Process for the preparation of (2r,3s)-3-phenylisoserine methyl ester acetate salt
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Page/Page column 5; 6, (2008/12/08)
A process for the enantioselective preparation of (2R,3S)-3-phenylisoserine methyl ester acetate salt of formula (I) which is an useful building block for the synthesis of taxane derivatives. The process involves the resolution of racemic threo-phenylisoserine amide and its conversion into (I).
A simple route to syn α-amino-β-hydroxy-esters by C-2 regioselective opening of α,β-epoxy esters with metal halides
Righi,Rumboldt,Bonini
, p. 13401 - 13408 (2007/10/02)
α,β-Epoxy esters are opened by NaX (X=I, Br) in a regio and stereoselective fashion to β-hydroxy-α-halo esters, which represent suitable precursors of syn α-amino-β-hydroxy esters and β-hydroxy esters.
Selective Additions of Gaseous Hydrochloric Acid to Crystalline Epoxides und Steroid-Epoxides
Kaupp, Gerd,Ulrich, Anke,Sauer, Gerhard
, p. 383 - 390 (2007/10/02)
Solid epoxides add gaseous HCl or KBr regioselectively and without melting, if the melting points are sufficiently high.Such additions proceed diastereoselectively with chiral epoxides.These gas/solid reactions are compared to similar transformations in solution.One observes interesting reaction sequences in the conversions of steroidal epoxides.Thus the opening of the epoxide ring may be followed by cationic rearrangements, or it occurs elimination od water, if it creates conjugation to a carbonyl group.
