93711-85-4

Basic information

• Product Name: (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(RS)-1-(hydroxycarbonyl)ethyl]-2-azetidinone
• CAS NO: 93711-85-4
• Molecular Weight: 301.458
• Mol File: 93711-85-4.mol

Chemical Properties

• Boiling Point: 424.4±10.0 °C(Predicted)
• Density: 1.050±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(RS)-1-(hydroxycarbonyl)ethyl]-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(RS)-1-(hydroxycarbonyl)ethyl]-2-azetidinone(93711-85-4)
• EPA Substance Registry System: (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(RS)-1-(hydroxycarbonyl)ethyl]-2-azetidinone(93711-85-4)

Safety Data

• Hazardous Substances Data: 93711-85-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(RS)-1-(hydroxycarbonyl)ethyl]-2-azetidinone is used as a building block for the synthesis of more complex organic molecules, taking advantage of its unique molecular structure and functional groups to create a diverse range of compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(RS)-1-(hydroxycarbonyl)ethyl]-2-azetidinone is used as a potential drug candidate due to its specific properties and interactions with biological systems. The stereochemistry of the compound, particularly the (3S,4S) configuration, is crucial for its effectiveness and selectivity in targeting specific biological pathways.
Used in Pharmaceutical Industry:
(3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(RS)-1-(hydroxycarbonyl)ethyl]-2-azetidinone is used as an intermediate in the development of new pharmaceuticals, leveraging its unique structural features to design and synthesize novel therapeutic agents with improved efficacy and selectivity.
Used in Research and Development:
(3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(RS)-1-(hydroxycarbonyl)ethyl]-2-azetidinone is also utilized in research and development settings to study its properties, reactivity, and potential applications in various chemical and biological processes. Understanding its behavior can lead to the discovery of new reactions and the development of innovative synthetic strategies.

Upstream product

• 96613-71-7 4(R)-<1-buten-3(S)-yl>-3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxoazetidine 
• 111187-44-1 3-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-4-<2-(1-hydroxy-2-methylethyl)>azetidin-2-one 
• 104420-08-8 (5R,6R,7S)-2,2-Dimethyl-7-[(1'R)-1'-Hydroxyethyl]-5-Methyl-8-Oxo-3-Oxa-1-Azabicyclo[4.2.0]Octane 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 150193-38-7 (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[1,1-di(allyloxycarbonyl)ethyl]-2-azetidinone 
• 158299-15-1 3-<(2R)-2-<(2R,3S)-3-<(1R)-1-(tert-Butyldimethylsiloxy)ethyl>-4-oxoazetidin-2-yl>propionyl>spiro-<2,3-dihydro-4H-1,3-benzoxazine-2,1'-cyclohexan>-4-one 
• 922733-34-4 C₂₃H₄₃NO₈Si 
• 108234-01-1 (3S,4R)-3-<(1R)-1-tert-butyldimethylsiloxyethyl>-4-(1-methoxycarbonylethylene)azetidin-2-one 
• 105320-12-5 2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-phenylselanyl-propionic acid methyl ester 
• 105320-12-5 (S)-2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-phenylselanyl-propionic acid methyl ester 
• 929112-78-7 (3S,4R)-3-((R)-1-tert-butyldimethylsilyloxyethyl)-1-butyryl-4-((R)-1-carboxyethyl)-2-azetidinone 
• 85260-51-1 N-propanoyl-1,3-thiazolidine-2-thione 
• 76855-69-1 Acetic acid (R)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl ester 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 

Downstream Products

• 202993-90-6 (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(R)-3-(4-methoxy-benzyloxy)-1-methyl-2-oxo-propyl]-azetidin-2-one 
• 90822-22-3 (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one 
• 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 
• 83973-55-1 (2R,4R,5R,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester 
• 83973-55-1 (2R,4S,5R,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester 
• 135096-42-3 (R)-benzyl 2-((2S,3S)-3-((1S)-1-hydroxyethyl)-4-oxoazetidin-2-yl)propanoate 
• 104873-15-6 4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]-heptane-2-carboxylate 
• 93711-81-0 (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 96036-03-2 meropenem 

Relevant articles and documents

Preparation method of meropenem intermediate 4-BMA

The invention provides a preparation method of a meropenem intermediate 4-BMA. Low-reaction-activity propionyl spirobenzoxazine cyclohexane is adopted, the meropenem intermediate 4-BMA is prepared through Reformatsky reaction and hydrolysis reaction in sequence, and in the preparation process, side reactions participating in reaction are few, further obtained product impurities are less, and the prepared 4-BMA is high in purity. In addition, the propionyl spirobenzoxazine cyclohexane is adopted as a raw material, the reaction yield is not affected, on the contrary, the reaction yield is greatly improved, and high reaction yield is obtained. Further, the adopted synthetic process is simple, post-treatment is convenient and easy to operate, the raw material and a catalyst are cheap and easy to obtain, safe and environmentally friendly, and the preparation cost is low. An experimental result shows that the mole yield of the prepared meropenem intermediate 4-BMA is 90.0% or above, and the purity is 98.5% or above.

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.

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.

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

IMPROVED METHOD FOR CRYSTALLIZATION OF AZETIDINONECARBOXYLIC ACID

The present invention relates to a method for crystallization of (2R)-2-{(3S,4S)-3-[(1R)-1-(tert-butyldimethylsilyloxy) ethyl]-2-oxoazetidin-4-yl}propionic acid, and is characterized in that crystallization is carried out by mixing a solution containing the compound with a substituted aromatic hydrocarbon solvent and/or a halogenated hydrocarbon solvent. The method can provide a crystal of the compound with a high purity and a high yield while the content of 2S isomer is kept at a low level.

PROCESS FOR STEREOSELECTIVE PREPARATION OF 4-BMA USING A CHIRAL AUXILIARY

The present invention relates to a process for preparing (3R,4S)-3-[[[R]-V-t- butyldimethylsilyloxy] ethyl] -4- [(/?)- l"-carboxyethyl]-2-azetidinone [4-BMA: formula (6)], 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-Valinol, and then the preparation of 4-BMA in high yield and high selectivity, under industrially mild conditions.

SYNTHESIS INTERMEDIATE FOR 1β-METHYLCARBAPENEM DERIVATIVE AND METHOD FOR PRODUCING SAME

Disclosed is a low-cost method for producing a 1β-methylcarboxylic acid (A) which is an important intermediate for providing a 1β-methylcarbapenem derivative at low cost. Also disclosed is such an intermediate. By compounds represented by the general formulae (I), (II) and (III) below and a method for producing a 1β-methylcarboxylic acid (A) wherein such compounds are used, a 1β-methylcarboxylic acid (A) as an important intermediate of a 1β-methylcarbapenem derivative can be synthesized from a low-cost, natural L-threonine.

Stereoselective mannich-like reactions of ester enolates generated on sugar templates: A novel access to a key intermediate for 1β-methylcarbapenem synthesis

The Mannich-like reactions of the enolates generated from 2,3-di-O-protected 6-deoxy-4-O-propionyl-α-D-glucopyranosides with (3R,4R)-4-acetoxy-3-((R)-1-(t-butyldimethylsilyloxy)ethyl ]azetidin-2-one were investigated. The corresponding 2,3-di-O-methyl derivative provided the Mannich adduct in good to excellent stereoselectivity. From the major adduct, the azetidin-2-one incorporating an α-methyl acetic acid side chain at the C-4 position with ?-configuration was obtained by alkaline hydrolysis. This product, (3S,4S)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl 1-4-1(R)-1-carboxyethylJazetidin-2-one, is a useful intermediate for the 1 ?-methylcarbapenem synthesis.