145041-34-5

Upstream product

• 133756-18-0 S-tert-butyl 2-(benzyloxy)ethanethioate 
• 145041-33-4 S-tert-butyl (2R,3R)-2-benzyloxy-3-hydroxy-3-phenylpropanethioate 

Downstream Products

• 154136-24-0 S-tert-butyl (2R,3S)-2-benzyloxy-3-tert-butoxycarbonylamino-3-phenylpropanethioate 
• 154136-25-1 methyl (2R,3S)-2-benzyloxy-3-tert-butoxycarbonylamino-3-phenylpropanoate 
• 145041-36-7 S-tert-butyl (2R,3S)-3-benzoylamino-2-benzyloxy-3-phenylpropanethioate 
• 145041-37-8 methyl (2R,3S)-3-benzoylamino-2-benzyloxy-3-phenylpropanethioate 
• 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 
• 145041-35-6 (2R,3S)-3-Amino-2-benzyloxy-3-phenyl-thiopropionic acid S-tert-butyl ester 

Relevant academic research and scientific papers

An optically active chromium(0)-complexed benzaldehyde in organic synthesis: A highly stereocontrolled asymmetric synthesis of (2R,3S)-(-)-N-benzoyl-3-phenylisoserine methyl ester, the taxol C-13 side chain analogue

An asymmetric aldol reaction of (+)-chromium(0)-complexed benzaldehyde 4 with the titanium enolate generated from the ethanethioate 5 provided the anti-aldol product 6 in a highly stereoselective manner, which was subsequently converted to the taxol C-13 side chain.

Highly stereocontrolled asymmetric syntheses of taxol and taxotere C-13 side chain analogues

Asymmetric aldol reaction of (+)-tricarbonyl(η6-2-trimethylsilylbenzaldehyde)chromium(0) complex (4) with titanium enolate of S-tert-butyl benzyloxyethanethioate (10) provided, after consecutive desilylation and decomplexation, anti-aldol product 15 in a highly stereo selective manner. Anti-product 15 was subsequently converted to (2R,3S)-N-benzoyl- and N-tert-butoxycarbonyl-3-phenylisoserine methyl esters (23 and 24), C-13 side chain analogues of taxol (1) and taxotere (2).