153463-32-2

Usage

Uses

Used in Chemical Synthesis:
2,3-Azetidinedione, 4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)-, (4S)is used as a building block in chemical synthesis for the creation of more complex organic molecules. Its unique structure allows it to participate in various reactions, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 2,3-Azetidinedione, 4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)-, (4S)is used as a key intermediate in the development of new drugs. Its specific functional groups can be exploited to design molecules with desired biological activities, potentially leading to the discovery of novel therapeutic agents.
Used in Material Science:
2,3-Azetidinedione, 4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)-, (4S)may also find applications in material science, where it could be used to develop new polymers or other materials with specific properties. Its ability to participate in various chemical reactions could enable the creation of materials with tailored characteristics for use in various industries.

Upstream product

• 185414-14-6 cis-3-allyloxy-2-azetidinone 
• 103239-04-9 N-(p-anisyl)-4-<(S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-methylene-imine 
• 104-94-9 4-methoxy-aniline 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 153463-28-6 (R)-3-[(2R,3R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-(4-methoxy-phenyl)-4-oxo-azetidin-3-yl]-4-phenyl-oxazolidin-2-one 
• 103174-02-3 (3R,4S)-cis-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 
• 141781-24-0 [1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine 
• 13831-31-7 Acetoxyacetyl chloride 
• 115828-87-0 (3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 

Downstream Products

• 220574-31-2 (3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolanyl-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propenyl)-2-azetidinone 
• 276244-09-8 (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-3-(1-methyl-1,2-propadienyl)-1-(p-methoxyphenyl)-2-azetidinone 
• 276244-14-5 (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-3-(1-phenyl-1,2-propadienyl)-1-(p-methoxyphenyl)-2-azetidinone 
• 358973-69-0 (3R,4S)-3-(1,1-Dimethyl-allyl)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one 
• 412272-08-3 (3R,4S)-3-(1,3-butadien-2-yl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-2-azetidinone 
• 665020-66-6 (3R,4S)-3-(2-bromoallyl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-2-azetidinone 

Relevant academic research and scientific papers

Straightforward Asymmetric Entry to Highly Functionalized 3-Substituted 3-Hydroxy-p-lactams via Baylis-Hillman or Bromoallylation Reactions

The reaction of various activated vinyl systems, including 2-cyclopenten-1-one, with enantiopure azetidine-2,3-diones 1 was promoted by DABCO to afford the corresponding optically pure Baylis-Hillman adducts 2 without detectable epimerization. However, th

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

Indium-promoted acyloxyallylation reaction of azetidine-2,3-diones in aqueous media: A new route to densely functionalized 3-substituted 3-hydroxy-β-lactams

Densely functionalized 3-substituted 3-hydroxy-β-lactams have been obtained by acyloxyallylation reaction of azetidine-2,3-diones with 3-bromopropenyl acetate or benzoate in aqueous media promoted by indium under Barbier conditions. Two new stereocenters were formed; the stereochemistry at the new C-3 quaternary center was fully controlled by placing a bulky chiral substituent at C-4. However, poor diastereoselectivities were observed in the new allylic stereocenter formed (up to 58% de). Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

N1-C4 β-lactam bond cleavage in the 2-(trimethylsilyl)thiazole addition to β-lactam aldehydes: Asymmetric synthesis of spiranic and tertiary α-alkoxy-γ-keto acid derivatives

Starting substrates, enantiopure spiranic or 3-substituted 3-alkoxy-4-oxoazetidine-2-carbaldehydes, were prepared from (R)-2,3-O- isopropylideneglyceraldehyde derived azetidine-2,3-diones by sequential Barbier-type addition reactions followed by hydroxy f

A novel one-step approach for the preparation of α-amino acids, α-amino amides, and dipeptides from azetidine-2,3-diones

A remarkable reaction of azetidine-2,3-diones with primary as well as secondary amines, and water is presented. Simply by varying the nucleophile, an unprecedented one-step synthesis of α-amino acids, α-amino amides, and dipeptides, was developed in both

Metal-mediated carbonyl-1,3-butadien-2-ylation by 1,4-bis(methanesulfonyl)-2-butyne or 1,4-dibromo-2-butyne in aqueous media: Asymmetric synthesis of 3-substituted 3-hydroxy-β-lactams

Metal-mediated 1,3-butadien-2-ylation reactions between 1,4-dibromo-2-butyne or 1,4-bis(methane-sulfonyl)-2-butyne and optically pure azetidine-2,3-diones were investigated in aqueous media, offering a convenient asymmetric entry to the potentially bioactive 3-substituted 3-hydroxy-β-lactam moiety. The diastereoselectivity of the addition reaction was controlled by the bulky chiral auxiliary at C4. However, while the regioselectivity of the process was full, the chemical yield of the addition was a function of the nature of both the metal reagent and the system solvent as well. In addition, 2-azetidinone-tethered 1,3-butadienes can easily be transformed into other functionalities via Diels-Alder reaction.

Metal-promoted allylation, propargylation, or allenylation of azetidine-2,3-diones in aqueous and anhydrous media. Application to the asymmetric synthesis of densely functionalized 3-substituted 3-hydroxy-β-lactams

Metal-mediated carbonyl allylation, allenylation, and propargylation of optically pure azetidine-2,3-diones were investigated in both anhydrous and aqueous environments. Different metals promoters showed varied regioselectivities on product formation duri

Asymmetric synthesis of α-keto β-lactams via [2+2] cycloaddition reaction: A concise approach to optically active α-hydroxy β-lactams and β-alkyl(aryl)isoserines

The cycloaddition reaction of the Evans-Sjogren ketenes to imines, followed by α-hydroxylation of the resulting cycloadducts provides an efficient general asymmetric synthesis of α-keto β-lactams and derivatives.