184302-65-6

Basic information

• Product Name: (S)-4-Oxo-4-phenyl-2-(toluene-4-sulfonylamino)-butyric acid tert-butyl ester
• Synonyms: (S)-4-Oxo-4-phenyl-2-(toluene-4-sulfonylamino)-butyric acid tert-butyl ester
• CAS NO: 184302-65-6
• Molecular Weight: 403.499
• Mol File: 184302-65-6.mol

Chemical Properties

• CAS DataBase Reference: (S)-4-Oxo-4-phenyl-2-(toluene-4-sulfonylamino)-butyric acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-Oxo-4-phenyl-2-(toluene-4-sulfonylamino)-butyric acid tert-butyl ester(184302-65-6)
• EPA Substance Registry System: (S)-4-Oxo-4-phenyl-2-(toluene-4-sulfonylamino)-butyric acid tert-butyl ester(184302-65-6)

Safety Data

• Hazardous Substances Data: 184302-65-6(Hazardous Substances Data)

Upstream product

• 71-43-2 benzene 
• 21440-07-3 (-)-(3S)-3,4-dihydro-3-(tosylamino)furan-2,5-dione 
• 181770-37-6 (S)-4-Oxo-4-phenyl-2-(toluene-4-sulfonylamino)-butyric acid 
• 115-11-7 isobutene 

Relevant articles and documents

154. Asymmetric synthesis of 3-hydroxyprolines by photocyclization of C(1′)-substituted N-(2-benzoylethyl)glycine esters

The chiral N-(2-benzoylethyl)-N-tosylglycine esters 5a-h and the α -amino-γ-keto ester 6 were prepared from γ-(tosylamino) alcohols 7a-h. Irradiation of compounds 5a-c, e gave cis-3-hydroxyproline esters 20-23 (Scheme 6), partly with complete asymmetric induction by the C(1′)-substituent, whereas 6 gave enantiomerically pure 4-hydroxy-4-phenyl-L-proline esters 24 in good yield but low de (Scheme 6). The de of the photocyclization depended on the nature and/or size of the C(1′)-substituents. Irradiation of ketones 5d and 5f, bearing H-atoms at C(γ) with respect to the keto function, gave cyclobutanols (Scheme 9) in low yields besides the preferred Norrish-type-II cleavage product. Cyclopentanol 25 was a by-product of the photocyclization of 5c as a result of H-C(δ) abstraction from the t-Bu group The structure of products 20, 22, and 24a, b was established by NMR or X-ray analyses.