97101-07-0

Basic information

• Product Name: (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one
• Synonyms: (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one
• CAS NO: 97101-07-0
• Molecular Weight: 301.458
• Mol File: 97101-07-0.mol
• Article Data: 53

Chemical Properties

• Boiling Point: 424.4±10.0 °C(Predicted)
• Density: 1.050±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one(97101-07-0)
• EPA Substance Registry System: (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one(97101-07-0)

Safety Data

• Hazardous Substances Data: 97101-07-0(Hazardous Substances Data)

Usage

Description

(3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one is a complex chiral molecule featuring an azetidin-2-one ring with specific substituents and stereochemistry, which may offer potential applications in various chemical industries.

Uses

Used in Organic Synthesis:
(3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one is used as a synthetic intermediate for the creation of more complex molecules, leveraging its unique structure and reactivity.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one is used as a key component in the development of novel drugs, potentially targeting various therapeutic areas due to its stereochemical complexity and functional group diversity.
Used in Chemical Research:
(3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one serves as a valuable compound in chemical research, particularly in the study of stereochemistry, asymmetric synthesis, and the development of new synthetic methodologies.

Upstream product

• 108772-91-4 2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-acrylic acid 
• 28562-53-0 4-acetoxy azetidinone 
• 1332594-11-2 3-(2-chloro-1-oxopropyl)spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one 
• 1224732-95-9 C₂₄H₄₃N₃O₅Si 
• 929112-78-7 (3S,4R)-3-((R)-1-tert-butyldimethylsilyloxyethyl)-1-butyryl-4-((R)-1-carboxyethyl)-2-azetidinone 
• 75517-65-6 (5R,6R,7S)-7-(1-Hydroxy-ethyl)-2,2,5-trimethyl-3-oxa-1-aza-bicyclo[4.2.0]octan-8-one 
• 127626-98-6 (4S)-N-(tert-butyldimethylsilyl)-4-<1-(hydroxymethyl)vinyl>-azetidin-2-one 
• 127627-00-3 (4S)-N-(t-butyldimethylsilyl)-4-<(1R)-(1-hydroxymethyl)ethyl>-azetidin-2-one 
• 127626-95-3 (4S)-N-(tert-butyldimethylsilyl)-4-<1-hydroxy-1-(methyl)ethyl>-azetidin-2-one 
• 127626-96-4 1-<(1,1-dimethylethyl)dimethylsilyl>-4-(1-methylethenyl)azetidin-2-one 
• 137063-74-2 (6S)-1-aza-3-oxa-2,2-dimethyl-4-methylenebicyclo<4.2.0>octan-8-one 
• 75521-16-3 (6S,5R)-1-aza-3-oxa-2,2,5-trimethylbicyclo<4.2.0>octan-8-one 
• 127626-99-7 (S)-4-(1-Hydroxymethyl-vinyl)-azetidin-2-one 
• 127708-14-9 (4S)-4-<(R)-1-(hydroxymethyl)ethyl>azetidine-2-one 

Downstream Products

• 83973-53-9 (S)-4-[(2R,3S)-3-(1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-pentanoic acid 4-nitro-benzyl ester 
• 357341-53-8 S-[(2R,3R)-tetrahydro-2-[[[(S)-3-methyl-2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]-1-oxobutyl]amino]methyl]-3-furanyl](α,2S,3S)-3-[(R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-α-methyl-4-oxo-2-azetidinemethanethiolate 
• 101135-08-4 (4S,5S,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-ylsulfanyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 90776-59-3 (4S,5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 101135-09-5 1-α-methyl RS-533 
• 101151-51-3 (4R,5S,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 90776-59-3 (4R,5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 101135-09-5 1-β-methyl RS-533 
• 263020-28-6 C₃₃H₅₂N₃O₁₀PSSi 
• 263020-25-3 C₃₃H₅₂N₃O₁₁PSSi 
• 263020-24-2 (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-1-[[(p-nitrobenzyl)oxy]oxalyl]-4-[(R)-1-[[(R)-2-oxopyrrolidin-4-ylthio]carbonyl]ethyl]-2-azetidinone 
• 96035-98-2 (3S,4S)-4-<(1R)-1-benzyloxycarbonylethyl>-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-2-azetidinone 
• 135096-42-3 (R)-benzyl 2-((2S,3S)-3-((1S)-1-hydroxyethyl)-4-oxoazetidin-2-yl)propanoate 
• 135038-17-4 (R)-benzyl 2-((2S,3S)-3-((R)-1-hydroxyethyl)-4-oxoazetidin-2-yl)propanoate 

Relevant articles and documents

Preparation method for synthesizing key intermediate 4-BMA of 1beta-methyl carbapenem antibiotic bicyclic nucleus

The invention relates to a preparation method for synthesizing a key intermediate 4-BMA of 1beta-methyl carbapenem antibiotic bicyclic nucleus and belongs to the technical field of synthesis of carbapenem antibiotics. The method disclosed by the invention comprises the following steps: taking an aqueous solution of tetrahydrofuran as a solvent, taking indium as a catalyst, taking (3R,4R)4-carbethoxy-3-[(R)-((tert-butyldimethylsilyl)oxy)ethyl]-2-2-azetidinone (IV) as a raw material, and carrying out a reaction with alpha-bromo-acrylamide XV with large inductive groups so as to produce a compound XIV; not separating the reaction solution of the compound XIV, and performing oxidation-hydrolysis, thereby obtaining the target product VI. The method disclosed by the invention is stable in process, short in reaction route, simple and convenient in operation, mild in reaction conditions, high in product purity, few in three wastes, low in cost, high in yield and suitable for large-scale industrial production.

1,3 IMIDAZOLIDINE DERIVATIVES AND THEIR USE IN THE PRODUCTION OF CARBAPENEM

Preparation of new heterocyclic compounds characterised by 1,3-imidazolidine structure useful for stereoselective synthesis of optically pure key intermediates in 1β-methylcarbapenem production

Method for manufacturing stereoselective preparation of 4-bma using a chiral auxiliary and chiral auxiliary

The present invention relates to a process for preparing (3R,4S)-3-[[[R]-1 ' -t-butyldimethylsilyloxy ]ethyl]-4-[(R)-1 "-carboxyethyl]-2-azetidinone (beta- methylazetidin-2-one; 4-BMA), a key intermediate for the synthesis of carbapenem and penem antibiotics. Specifically, the present invention relates to a process comprising first, the preparation of a chiral auxiliary from cheap L-Phenylalaninol, and then the preparation of 4-BMA in high yield and high selectivity, under industrially mild condition.