90776-58-2

Usage

Chemical Properties

White powder mp 146-147°C LOD ≤0.1%

Uses

Harmful by inhalation and in contact with skin

InChI:InChI=1/C14H27NO4Si/c1-8(13(17)18)11-10(12(16)15-11)9(2)19-20(6,7)14(3,4)5/h8-11H,1-7H3,(H,15,16)(H,17,18)/t8-,9-,10-,11-/m1/s1

Upstream product

• 77877-19-1 N-isopropyl oxazolidinone 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 117481-95-5 (3S,4S)-3-[(R)-t-butyldimethylsilyloxyethyl]-4-{(R)-1-[(3-methylpyridin-2-2ylmethylthio)carbonyl]ethyl}azetidin-2-one 
• 105320-15-8 (3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(1-hydroxymethyl-vinyl)-azetidin-2-one 
• 105320-16-9 (6S,7S)-7-((R)-1-tert-butyldimethylsilyloxyethyl)-2,2-dimethyl-5-methylene-(3-oxa-1-aza-bicyclo[4.2.0]octane-8-one) 
• 114341-91-2 (3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(R)-1-(4,4-dimethyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 114418-65-4 (3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(S)-1-(4,4-dimethyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 127680-59-5 (3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(R)-1-(4,4-dibutyl-5,5-pentamethylene-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 127759-35-7 (3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(S)-1-(4,4-dibutyl-5,5-pentamethylene-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 114341-78-5 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-(2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 114341-95-6 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-(4,4,5,5-tetramethyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 114341-85-4 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-((R)-4-phenyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 109715-77-7 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-((S)-4-benzyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 28562-53-0 4-acetoxy azetidinone 

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 
• 153471-17-1 (4R,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(diphenoxy-phosphoryloxy)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 
• 184223-77-6 (4S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[1,3]dithian-2-ylidene-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 184223-76-5 [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((S)-2-[1,3]dithian-2-ylidene-1-methyl-ethyl)-4-oxo-azetidin-1-yl]-hydroxy-acetic acid benzhydryl ester 
• 153893-57-3 pivaloyloxymethyl (1R,5R,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-(diphenylphosphoryloxy)-1-methylcarbapen-2-em-3-carboxylate 
• 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 

Relevant academic research and scientific papers

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.

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.

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.

A PROCESS FOR THE PREPARATION OF THE INTERMEDIATE OF Β-METHYL CARBAPENEM

A process of preparation of the intermediate of β-methyl carbapenem is disclosed, in which 4-acetylazacyclobutanone as the raw material is firstly reacted with α-bromopropionamide having a big inductive group. Since this reaction is highly stereoselectivity, most of the product is the required parent nucleus of β-methyl carbapenem, a product of β-configuration. Compared with the prior art, the process of the present invention is highly-yielding, cost-effective and can be used for large scale production.

A PROCESS FOR THE PREPARATION OF MEROPENEM

The invention relates to a process for the preparation of meropenem, a β-methylcarbopenem. The said process comprises the following steps: preparing the compound of Formula (XI) from the compound of Formula (IV) through three steps "one-pot process"; then condensing the compound of Formula (XI) with the compound of Formula (XX) to form the compound of Formula (XXIV); finally preparing meropenam of Formula (I) from the compound of Formula (XXIV) by deprotection reaction by means of catalyst. The process of the invention is easily to carry out, the product is isolated in high content and yield, and the cost is reduced, thereby overcoming the shortage of the prior art.