144465-78-1

Basic information

• Product Name: 2-Azetidinone, 1-(4-methoxyphenyl)-4-phenyl-3-[[tris(1-methylethyl)silyl]oxy]-, (3R,4S)-
• CAS NO: 144465-78-1
• Molecular Formula: C25H35NO3Si
• Molecular Weight: 425.643
• Mol File: 144465-78-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Azetidinone, 1-(4-methoxyphenyl)-4-phenyl-3-[[tris(1-methylethyl)silyl]oxy]-, (3R,4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone, 1-(4-methoxyphenyl)-4-phenyl-3-[[tris(1-methylethyl)silyl]oxy]-, (3R,4S)-(144465-78-1)
• EPA Substance Registry System: 2-Azetidinone, 1-(4-methoxyphenyl)-4-phenyl-3-[[tris(1-methylethyl)silyl]oxy]-, (3R,4S)-(144465-78-1)

Safety Data

• Hazardous Substances Data: 144465-78-1(Hazardous Substances Data)

Upstream product

• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 13154-24-0 triisopropylsilyl chloride 
• 104-94-9 4-methoxy-aniline 
• 100-52-7 benzaldehyde 
• 146924-94-9 (3R,4S)-(+)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 94612-33-6 1-(4-methoxyphenyl)-4-phenylazetidine-2,3-dione 
• 194234-97-4 3-Hydroxy-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 
• 186613-02-5 cis-1-p-methoxyphenyl-3-acetoxy-4-phenylazetidin-2-one 
• 132127-27-6 (1R,2S)-2-phenyl-1-cyclohexyl<(triisopropylsilyl)oxy>acetate 

Downstream Products

• 209110-50-9 (3R,4S)-3-(Dimethyl-phenyl-silanyloxy)-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 
• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 
• 209110-73-6 (3R,4S)-3-Allyl-3-(dimethyl-phenyl-silanyloxy)-2-oxo-4-phenyl-azetidine-1-carboxylic acid tert-butyl ester 
• 209110-58-7 (3R,4S)-3-Allyl-3-(dimethyl-phenyl-silanyloxy)-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 
• 209110-70-3 (3R,4S)-3-(Dimethyl-phenyl-silanyloxy)-3-methyl-2-oxo-4-phenyl-azetidine-1-carboxylic acid tert-butyl ester 
• 209110-55-4 (3R,4S)-3-(Dimethyl-phenyl-silanyloxy)-1-(4-methoxy-phenyl)-3-methyl-4-phenyl-azetidin-2-one 
• 209110-63-4 (3R,4S)-3-Allyl-3-(dimethyl-phenyl-silanyloxy)-4-phenyl-azetidin-2-one 
• 209110-60-1 (3R,4S)-3-dimethylphenylsilyloxy-3-methyl-4-phenyl-β-lactam 
• 182155-36-8 (3R,4S)-3-hydroxy-3-methyl-4-phenyl-β-lactam 
• 168416-37-3 (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-2-methyl-3-phenylpropionic acid methyl ester 
• 618428-02-7 2'-triisopropylsilyl-7-triethylsilylpaclitaxel 

Relevant articles and documents

Ni-Catalyzed asymmetric reduction of α-keto-β-lactams: via DKR enabled by proton shuttling

Chiral α-hydroxy-β-lactams are key fragments of many bioactive compounds and antibiotics, and the development of efficient synthetic methods for these compounds is of great value. The highly enantioselective dynamic kinetic resolution (DKR) of α-keto-β-lactams was realized via a novel proton shuttling strategy. A wide range of α-keto-β-lactams were reduced efficiently and enantioselectively by Ni-catalyzed asymmetric hydrogenation, providing the corresponding α-hydroxy-β-lactam derivatives with high yields and enantioselectivities (up to 92% yield, up to 94% ee). Deuterium-labelling experiments indicate that phenylphosphinic acid plays a pivotal role in the DKR of α-keto-β-lactams by promoting the enolization process. The synthetic potential of this protocol was demonstrated by its application in the synthesis of a key intermediate of Taxol and (+)-epi-Cytoxazone. This journal is

New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method

Highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with excellent enantiomeric purity is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenyl-isoserine and its analogs. (3R,4S)-N-benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone readily derived from the 3-hydroxy-4-phenyl-β-lactam is coupled with protected baccatin IIIs, followed by deprotection to give optically pure taxol and 10-deacetyl-7,10-bis(Troc)-taxol in good yields. Fully assigned 1H, 13C, and 2D (COSY and HETCOR) NMR spectra of taxol thus synthesized are shown and discussed.