145438-00-2

Upstream product

• 19190-80-8 methyl trans-3-phenylglycidate 
• 32803-73-9 methyl 3-phenyl-3-chloro-2-ketopropionate 
• 100-52-7 benzaldehyde 
• 19190-80-8 cis-methyl 2,3-epoxy-3-phenylpropanoate 

Downstream Products

• 328402-02-4 (2R,3S)-2-Acetoxy-3-chloro-3-phenyl-propionic acid methyl ester 
• 328402-05-7 methyl (2S,3R)-3-chloro-2-hydroxy-3-phenylpropanoate 
• 19190-80-8 cis-methyl 2,3-epoxy-3-phenylpropanoate 
• 328402-04-6 methyl (2S,3S)-(+)-3-chloro-2-hydroxy-3-phenylpropanoate 
• 328402-07-9 methyl (2R,3R)-3-chloro-2-hydroxy-3-phenylpropanoate 
• 158830-39-8 methyl (2S,3S)-2-hydroxy-3-(N-tert-butoxycarbonylamino)-3-phenylpropanoate 
• 144541-45-7 methyl (2S,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 146848-91-1 (4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester 
• 99458-16-9 (2R,3S)-(+)-methyl 3-azido-2-benzoly-3-phenylpropionate 
• 129866-71-3 Methyl (2S,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate 
• 99528-65-1 (2R,3R)-(+)-methyl 3-phenyloxiranecarboxylate 
• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 99458-15-8 Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of the C-13 side chain of paclitaxel (Taxol) and docetaxel (Taxotere)

Reduction of methyl 3-chloro-2-oxo-3-phenylpropanoate with various reducing agents gave syn- and anti-3-chloro-2-hydroxy-3-phenylpropanoates 3, which underwent an efficient lipase-catalyzed resolution. All four diastereomers were subsequently converted to N-benzoyl-(2R,3S)-3-phenylisoserine methyl ester, C-13 side chain analogues of paclitaxel (Taxol).

N-Benzoyl-(2R,3S)-3-Phenylisoserine Methyl Ester; A Facile and Convenient Synthesis and Resolution by Entrainment

The importance of N-benzoyl (2R,3S)-phenylisoserine (3), also known as the "taxol side chain", for the strong antitumor activity of taxol (1), a potent anticancer drug, has prompted numerous efforts towards the development of a practical taxol side chain synthesis.Here we describe a highly practical and inexpensive synthesis of the taxol side chain methyl ester 4 and resolution via entrainment based on the observation that compound 4 exhibits conglomerate crystal structure.

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.