99458-16-9

Upstream product

• 99458-15-8 Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate 
• 98-88-4 benzoyl chloride 
• 32803-73-9 methyl 3-phenyl-3-chloro-2-ketopropionate 
• 99528-63-9 (2S,3R)-2,3-epoxy-3-phenylpropan-1-ol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 117486-25-6 (2R,3R)-(-)-methyl 3-bromo-2-hydroxy-3-phenylpropionate 
• 115794-67-7 methyl (2R,3S)-3-phenylglycidate 
• 104196-23-8 (2S,3S)-2,3-epoxy-3-phenyl-1-propanol 
• 328402-04-6 methyl (2S,3S)-(+)-3-chloro-2-hydroxy-3-phenylpropanoate 
• 145438-00-2 methyl (+/-)-syn-3-chloro-2-hydroxy-3-phenylpropanoate 
• 145438-00-2 methyl (+/-)-anti-3-chloro-2-hydroxy-3-phenylpropanoate 
• 100-52-7 benzaldehyde 
• 99528-65-1 (2R,3R)-(+)-methyl 3-phenyloxiranecarboxylate 
• 328402-05-7 methyl (2S,3R)-3-chloro-2-hydroxy-3-phenylpropanoate 

Downstream Products

• 99475-54-4 C₄₂H₅₁NO₁₀Si 
• 99458-27-2 C₃₆H₃₇NO₉ 
• 99458-24-9 (2R,3S)-3-Benzoylamino-2-benzyloxymethoxy-3-phenyl-propionic acid (3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester 
• 99458-26-1 (2R,3S)-3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid (3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester 
• 99458-23-8 (2R,3S)-3-Benzoylamino-2-methoxymethoxy-3-phenyl-propionic acid (1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester 
• 99458-19-2 (2R,3S)-N-benzoyl-O-<<2-(trimethylsilyl)ethoxy>methyl>-3-phenylisoserine methyl ester 
• 99458-18-1 (2R,3S)-N-benzoyl-O-<(benzyloxy)methyl>-3-phenylisoserine methyl ester 
• 99458-21-6 (2R,3S)-N-benzoyl-O-<(benzyloxy)methyl>-3-phenylisoserine 
• 99458-25-0 (2R,3S)-3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid (1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester 
• 99458-17-0 (2R,3S)-N-benzoyl-O-(methoxymethyl)-3-phenylisoserine methyl ester 
• 99458-20-5 (2R,3S)-N-benzoyl-O-(methoxymethyl)-3-phenylisoserine 
• 99458-22-7 (2R,3S)-N-benzoyl-O-<<2-(trimethylsilyl)ethoxy>methyl>-3-phenylisoserine 
• 132201-33-3 (2R,3S)-N-benzoyl-3-phenylisoserine 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 

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).

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.

An Efficient, Enantioselective Synthesis of the Taxol Side Chain

An asymmetric epoxidation (70-80percent ee) and a highly regioselective epoxide cleavage have been used as the key reactions in the synthesis of the taxol side chain methyl ester (2; 95percent ee, 23percent overall yield from phenylacetylene.Transesterifications of 2 (in four steps) have been effected and are exemplified with (-)-isopinocampheol (8), 1,2;3,4-di-O-isopropylidene-D-galactopyranose (9), and methyl gibberellate (10).