146924-94-9

Usage

Uses

Used in Pharmaceutical Industry:
(3R,4S)-3-Hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone is used as a key intermediate in the synthesis of the taxol side chain and its analogs. Taxol, a well-known chemotherapy drug, is used for the treatment of various types of cancer, including ovarian, breast, and lung cancer. The compound's unique structure allows it to serve as a building block for the development of new and improved cancer therapeutics.
Used in Chemical Synthesis:
In the field of chemical synthesis, (3R,4S)-3-Hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone can be utilized as a versatile starting material for the creation of a wide range of other organic compounds. Its functional groups and stereochemistry make it a valuable asset in the development of novel molecules with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C16H15NO3/c1-20-13-9-7-12(8-10-13)17-14(15(18)16(17)19)11-5-3-2-4-6-11/h2-10,14-15,18H,1H3

Upstream product

• 104-94-9 4-methoxy-aniline 
• 40339-42-2 4-methoxy-N-[(1Z)-phenylmethylene]aniline 
• 41625-51-8 trimethylsiloxyacetic acid 
• 19340-68-2 1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 
• 63160-12-3 2-[(4-methylphenyl)sulfonyl]-3-phenyl-oxaziridine 
• 94612-33-6 1-(4-methoxyphenyl)-4-phenylazetidine-2,3-dione 
• 131968-76-8 (+/-)-(3R,4S)-3-acetoxy-N-(4-methoxyphenyl)-4-phenylazetidin-2-one 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 186613-02-5 cis-1-p-methoxyphenyl-3-acetoxy-4-phenylazetidin-2-one 
• 194234-97-4 3-Hydroxy-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 100-52-7 benzaldehyde 
• 153463-27-5 (R)-3-[(3R,4S)-1-(4-Methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl]-4-phenyl-oxazolidin-2-one 
• 101067-78-1 (+/-)-(3R,4S)-3-hydroxy-4-phenyl-N-(4-methoxyphenyl)azetidin-2-one 

Downstream Products

• 162599-35-1 cis-1-(p-anisyl)-3'S-(4,6-diacetoxy-2,3-enyl-α-O-glycoside)-4R-phenyl-azetidin-2-one 
• 162458-86-8 cis-1-(p-anisyl)-3'R-(4,6-diacetoxy-2,3-enyl-α-O-glycoside)-4S-phenyl-azetidin-2-one 
• 94612-33-6 1-(4-methoxyphenyl)-4-phenylazetidine-2,3-dione 
• 146924-95-0 (-)-(3S,4R)-3-acetoxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one 
• 146924-90-5 (+)-cis-(3R,4S)-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 146924-94-9 (3R,4S)-(+)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 1415716-33-4 C₂₁H₂₅NO₄ 
• 1415716-25-4 cis-1-(p-Anisyl)-3'R-(4-acetoxy-5-hydro-2,3-dienyl-α-O-glycoside)-4S-phenyl-azetidin-2-one 
• 1415716-26-5 cis-1-(p-anisyl)-3'S-(4-acetoxy-5-hydro-2,3-dienyl-α-O-glycoside)-4R-phenyl-azetidin-2-one 

Relevant academic research and scientific papers

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

Synthesis and biological evaluation of novel larotaxel analogues

Taxoids are a class of successful drugs and have been successfully used in chemotherapy for a variety of cancer types. However, despite the hope and promises that these taxoids have engendered, their utility is hampered by some clinic limitations. Extensive structure-activity relationship (SAR) studies of toxoids have been performed in many different laboratories. Whereas, SAR studies that based on the new-generation toxoid, larotaxel, have not been reported yet. In view of the advantages in preclinical and clinical data of larotaxel over former toxoids, new taxoids that strategicly modified at the C3’/C3′-N and C2 positions of larotaxel were designed, semi-synthesized, and examined for their potency and efficacy in vitro. As a result, it has been shown that the majority of these larotaxel analogues are exceptionally potent against both drug-sensitive tumor cells and tumor cells with drug resistance arising from P-glycoprotein over expression. Further in vivo antitumor efficacies investigations revealed A2 might be a potent antitumor drug candidate for further preclinical evaluation.

Reactivity of 3-Oxo-β-lactams with Respect to Primary Amines—An Experimental and Computational Approach

The reactivity of 3-oxo-β-lactams with respect to primary amines was investigated in depth. Depending on the specific azetidin-2-one C4 substituent, this reaction was shown to selectively produce 3-imino-β-lactams (through dehydration), α-aminoamides (thr

A mild and selective reduction of β-lactams: Rh-catalyzed hydrosilylation towards important pharmacological building blocks

Four-membered N-heterocyclic compounds exhibit a broad range of pharmacological activities. Herein, we report a useful rhodium-catalyzed protocol for the activation of phenylsilane to reduce tertiary β-lactams. Reaction with the tertiary amides was select

Stereospecific novel glycosylation of hydroxy β-lactams via iodine-catalyzed reaction: A new method for optical resolution

Glycosylation of racemic and optically active α-hydroxy β-lactams by reaction with a few glycal derivatives in the presence of catalytic amounts of iodine has provided stereospecific formation of α-glycosides. This method has been extended for the prepara

A novel asymmetric synthesis of 3-(1H-pyrrol-1-yl)-substituted β-lactams via a bismuth nitrate-catalyzed reaction

The reaction of racemic α-keto β-lactams 5a-5c with the commercially available chiral compound trans-4-hydroxy-L-proline (6) in the presence of a catalytic amount of Bi(NO3)3·5 H 2O in EtOH gave a diastereoisomer mixture o

Arthrobacter sp.: a lipase of choice for the kinetic resolution of racemic arylazetidinone precursors of taxanoid side chains

The native strain of Arthrobacter sp. (MTCC 5125) bearing a lipase has been found to be the most effective in the kinetic resolution of racemic arylazetidinones for producing cis-(3R,4S)-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone, cis-(3R,4S)-3-

Reductive ring opening of 2-azetidinones promoted by sodium borohydride

Variously substituted 2-azetidinones 3 and 4 were reacted with sodium borohydride in aqueous isopropanol giving 3-aminopropan-1,2-dioles 5 and 7. Reaction extent was dependent upon the substitution pattern in the 3- and 4-positions of the 2-azetidinone ri

The dynamic kinetic resolution of 3-oxo-4-phenyl-β-lactam by recombinant E. coli overexpressing yeast reductase Ara1p

Using a recombinant E. coli strain overexpressing yeast reductase Ara1p, we reduced racemic 3-oxo-4-phenyl-β-lactam to cis-(3S,4R)-3-hydroxy-4-phenyl- β-lactam as a single enantiopure product. The dynamic kinetic resolution occurred over the course of fermentation at pH 7. Under the same conditions, 3-oxo-4-(2-thiophenyl)-β-lactam 4 and 3-oxo-4-(2-furyl)-β-lactam 5 were not resolved.

Application of newly available bio-reducing agents to the synthesis of chiral hydroxy-β-lactams: Model for aldose reductase selectivity

Homochiral 3-hydroxy-4-substituted β-lactams serve as precursors to the corresponding α-hydroxy-β-amino acids-key components of many biologically and therapeutically important compounds. We have developed a short synthetic sequence for these targets using