181294-27-9

Basic information

• Product Name: (2S,3S)-3-Benzoylamino-2-hydroxy-3-phenyl-thiopropionic acid S-phenyl ester
• Synonyms: (2S,3S)-3-Benzoylamino-2-hydroxy-3-phenyl-thiopropionic acid S-phenyl ester
• CAS NO: 181294-27-9
• Molecular Weight: 377.464
• Mol File: 181294-27-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2S,3S)-3-Benzoylamino-2-hydroxy-3-phenyl-thiopropionic acid S-phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-Benzoylamino-2-hydroxy-3-phenyl-thiopropionic acid S-phenyl ester(181294-27-9)
• EPA Substance Registry System: (2S,3S)-3-Benzoylamino-2-hydroxy-3-phenyl-thiopropionic acid S-phenyl ester(181294-27-9)

Safety Data

• Hazardous Substances Data: 181294-27-9(Hazardous Substances Data)

Upstream product

• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 144192-69-8 (tert-Butyl-dimethyl-silanyloxy)-thioacetic acid S-phenyl ester 

Downstream Products

• 186596-02-1 (4S,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carbothioic acid S-phenyl ester 
• 144541-45-7 methyl (2S,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 158722-23-7 7-(triethylsilyl)-13-O-[((4S,5R)-2,4-diphenyl-4,5-dihydrooxazol-5-yl)carbonyl]baccatin 
• 33069-62-4 taxol 
• 7309-55-9 (2S,3S)-N-benzoyl-3-phenylisoserine 

Relevant articles and documents

Taxol semisynthesis: A highly enantio- and diastereoselective synthesis of the side chain and a new method for ester formation at C-13 using thioesters

A very simple, new, and straightforward approach to the Paclitaxel (Taxol) and Docetaxel (Taxotere) side chains has been developed using the imine addition reaction of thioester-derived boron enolates bearing chiral ligands. The addition reaction was studied extensively, using a combination of different thioesters (ROCH2COSPh, ROCH2COSt-Bu), oxygen protecting groups (R = Bn, TBDMS, COPh, EE, TMS), chiral boron ligands [derived from both (-) and (+)-menthone], imines (PhCH=NSiMe3, PhCH=NCOPh), and in the presence or in the absence of additional Lewis acids (BF3-OEt2, Et2AlCl, TiCl4). The side chain was assembled in a few steps with the correct relative (syn) and absolute stereochemistry (2R,3S). The stereochemical outcome of the boron-mediated reaction was rationalized using chair vs boat transition state structures. A new direct route for attachment of the side chains to the baccatin nucleus using thioester chemistry has also been developed. By treatment of a mixture of a thioester (8, 12, or 17) and protected baccatin III (2b, 2c) with LHMDS, the 13-0 acylated compounds were obtained in high yield (up to 90%). Hydrolysis of 18b gave Paclitaxel (1a) in 80% yield.