117486-25-6

Upstream product

• 19190-80-8 methyl trans-3-phenylglycidate 
• 115794-67-7 methyl (2R,3S)-3-phenylglycidate 
• 104196-23-8 (2S,3S)-2,3-epoxy-3-phenyl-1-propanol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 19190-80-8 cis-methyl 2,3-epoxy-3-phenylpropanoate 

Downstream Products

• 99458-15-8 Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate 
• 99458-16-9 (2R,3S)-(+)-methyl 3-azido-2-benzoly-3-phenylpropionate 
• 132201-33-3 (2R,3S)-N-benzoyl-3-phenylisoserine 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 19190-80-8 cis-methyl 2,3-epoxy-3-phenylpropanoate 

Relevant academic research and scientific papers

Process for the preparation of (2r,3s)-3-phenylisoserine methyl ester acetate salt

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).

Synthesis of taxoids 4. Novel and versatile methods for preparation of new taxoids by employing cis- or trans-phenyl glycidic acid

A novel route to the synthesis of docetaxel using esterification of (2R,3R)-or (2R,3S)-glycidic acid with 7,10-bis-O-(2,2,2- trichloroethoxycarbonyl)-10-deacetylbaccatin III is described. Related novel taxoids which have new side chains were synthesized from these synthetic intermediates.

A simple route to syn α-amino-β-hydroxy-esters by C-2 regioselective opening of α,β-epoxy esters with metal halides

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.

Enantio- and stereo-selective route to the taxol side chain via asymmetric epoxidation of trans-cinnamyl alcohol and subsequent epoxide ring opening

The first route to the side chain of Taxol and Taxotere, employing asymmetric epoxidation (AE) of trans-cinnamyl alcohol and a new highly regio- and stereo-selective opening of the epoxide ring with MgBr2, is described.

Selective Additions of Gaseous Hydrochloric Acid to Crystalline Epoxides und Steroid-Epoxides

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.