103174-02-3

Basic information

• Product Name: (3R,4S)-cis-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
• Synonyms: (3R,4S)-cis-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
• CAS NO: 103174-02-3
• Molecular Weight: 335.357
• Mol File: 103174-02-3.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (3R,4S)-cis-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-cis-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one(103174-02-3)
• EPA Substance Registry System: (3R,4S)-cis-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one(103174-02-3)

Safety Data

• Hazardous Substances Data: 103174-02-3(Hazardous Substances Data)

Upstream product

• 13831-31-7 Acetoxyacetyl chloride 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 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 
• 153463-32-2 (S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)azetidine-2,3-dione 
• 185414-14-6 cis-3-allyloxy-2-azetidinone 
• 141781-24-0 [1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine 
• 103239-04-9 N-(p-anisyl)-4-<(S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-methylene-imine 
• 115828-87-0 (3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 
• 75-36-5 acetyl chloride 

Downstream Products

• 277330-95-7 (3S,4S)-trans-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 
• 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 
• 276244-06-5 (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propynyl)-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 
• 277758-04-0 methanesulfonate of (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone 
• 115828-84-7 (3R,4S)-cis-1-(p-anisyl)-3-(allyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 
• 221909-59-7 (+)-(3R,4R)-4-formyl-3-allyloxy-1-(p-methoxyphenyl)-2-azetidinone 
• 277757-73-0 (+)-(3R,4R)-3-(2-carboxymethyl-1-ethenyloxy)-4-formyl-1-(p-methoxyphenyl)-2-azetidinone 
• 277330-97-9 (+)-(3S,4R)-trans-1-(p-methoxyphenyl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2-azetidinone 
• 277757-84-3 (+)-(3R,4S)-3-allyloxy-1-(p-methoxyphenyl)-4-[(S)-1,2-dihydroxyethylen]-2-azetidinone 
• 277757-95-6 (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone 
• 277757-85-4 (+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-1,2-dihydroxyethylen]-1-(p-methoxyphenyl)-2-azetidinone 

Relevant articles and documents

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.

Stereoselective synthesis of-lactams under diverse conditions: Unprecedented Observations

ferent reaction conditions have been used for this study. It is important to note that the stereochemistry of the-lactam formation reaction depends on the conditions of the experiments, structures of the imines and acid chlorides, order of addition of the

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