35564-99-9

Upstream product

• 100-39-0 benzyl bromide 
• 24158-88-1 6,6-dibromopenicillanic acid 
• 139595-42-9 6,6-dibromopenicillanic acid 
• 15058-70-5 6-diazopenicillanic acid benzyl ester 
• 100-44-7 benzyl chloride 
• 100-51-6 benzyl alcohol 

Downstream Products

• 62263-85-8 (5R)-6c-bromo-6t-((R)-1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid benzyl ester 
• 62263-85-8 (5R)-6t-bromo-6c-((Ξ)-1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid benzyl ester 
• 90425-45-9 benzyl 6-bromo-6-(2-phenylsulphinyl-2-ethoxycarbonylethyl)penicillanate 
• 90425-52-8 (2S,5R)-6-(2-Benzenesulfinyl-2-dimethylcarbamoyl-ethyl)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 90425-42-6 (2S,5R)-6-(2-Benzenesulfinyl-3-oxo-3-phenyl-propyl)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 69979-55-1 (2S,5R,6S)-6-Bromo-6-(1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 76454-54-1 benzyl 6,6-dibromo-1,1-dioxopenicillanate 
• 62263-89-2 Benzyl 6α-bromopenicillanate 
• 71840-49-8 6β-bromopenicillanic acid benzyl ester 
• 62263-72-3 (2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 90425-37-9 benzyl 6-bromo-6-(1-hydroxy-1-phenylprop-2-ynyl)penicillanate 
• 76454-54-1 benzyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0]-heptane-2-carboxylate-4,4-dioxide 
• 76946-53-7 (2S,4R,5R)-3,3-Dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 303730-72-5 benzyl (2S)-2-[(4S)-4-chloro-2-oxazetidin-1-yl]-2-(1-chlorothio-1-methylethyl)-acetate 

Relevant academic research and scientific papers

A solid- and solution-phase-based library of 2β-methyl substituted penicillin derivatives and their effects on growth inhibition of tumor cell lines

We described the design, synthesis and antiproliferative properties of a series of twenty 2β-methyl substituted penicillin derivatives. This analysis includes evaluation against HeLa and MCF-7 human tumor cell lines and LM3 and B16-F0 murine tumor cell lines. The epithelial cell line derived from the normal mammary gland of mice (NMuMG) and the mouse embryo fibroblast cell line (3T3) were used as controls (non-cancer cells). This journal is

Syntheses of (6S)-cephalosporins from 6-aminopenicillanic acid

Two practical routes to (6S,7S)-cephalosporins from 6-aminopenicillanic acid (6-APA) are described. In the first, 6-APA was converted to (2S,4S,5S,6S)-penicillin sulfoxide 49, which underwent Morin ring expansion to a protected (6S,7S)-cephem 50. In the s

Butylstannonic acid catalyzed transesterification of carboxylic esters

Butylstannonic acid is used as catalyst for transesterification of various carboxylic eaters. This method is also applicable to acetylation/deacetylation of alcohols.

Synthesis Of 6β-Methoxy-6α-Hydroxymethylpenenms

6α-Hydroxymethyl-6β-methoxy-2-phenoxymethylpenem was synthesized from benzyl 6β-bromo-6α-methoxypenicillanate via radical addition at 6α-position of methyl tributyltinacrylate and tributyltinstyrene inter alia.The reaction sequence to penem proceeds via secopenicillanates according to established procedures.The good yield of the radical reaction and its stereoselectivity provide a useful entry to the 6α-substituted 6β-methoxypenems and in particular to the 6α-hydroxymethyl-6β-methoxypenems.

Carbapenams and carbapen-2-ems and process therefor

Carbapenam-3-carboxylic acids and carbapen-2-em-3-carboxylic acids substituted at the 1-position with an oxo, a hydroxy or an acetoxy group, variously substituted at the 2-position with such groups as methyl, acetoxymethyl, methanesulfonyloxy, alkoxy, alkylthio, aminoalkylthio or amidinoalkylthio and optionally substituted at the 6-position with a hydroxyalkyl group, an acetoxyalkyl group or a conventional penicillin side-chain, pharmaceutically-acceptable salts thereof and various esters thereof wherein the esterifying group is selectively removed in the laboratory, or hydrolyzed under physiological conditions. These compounds are useful either systemically or topically in the treatment of diseases caused by susceptible microorganisms, as animal feed additives for promotion of growth, or in the preservation of biodegradable materials, or as intermediates to compounds having such antibacterial activity. Key to the synthesis of these compounds is the light catalyzed rearrangement of 2-diazo-1-oxoceph-3-em-4-carboxylates to 1-oxocarbapen-2-em-3-carboxylates, a newly discovered reaction determined to be of general applicability.

Bis-esters of alkanediols as antibacterial agents

6-Acylaminopenicillanoyloxymethyl esters and 1-(6-acylaminopenicillanoyloxy)ethyl esters of 2-beta-acetoxymethyl-2-alpha-methyl-(5R)penam-3-alpha-carboxylic acid 1,1-dioxide are useful as antibacterial agents. The 6-aminopenicillanoyloxymethyl ester, the 1-(6-aminopenicillanoyloxy)ethyl ester and certain other mono-substituted methyl and ethyl esters of 2-beta-acetoxymethyl-2-alpha-methyl-(5R)penam-3-alpha-carboxylic acid 1,1-dioxide are useful intermediates to the aforesaid antibacterial agents.

ACETOXYMETHYL PENAM COMPOUNDS AS BETA-LACTAMASE INHIBITORS

2-beta-Acetoxymethyl-2-alpha-methyl-(5R)penam-3-alpha-carboxylic acid 1,1-dioxide, pharmaceutically-acceptable salts thereof and esters thereof readily hydrolyzable in vivo; pharmaceutical compositions containing 2-beta-acetoxymethyl-2-alpha-methyl-(5R)penam-3-alpha-carboxylic acid 1,1-dioxide or salt or ester thereof; and method of enhancing the effectiveness of a beta-lactam antibiotic using 2-beta-acetoxymethyl-2-alpha-methyl-(5R)penam-3-alpha-carboxylic acid 1,1-dioxide or salt or ester thereof

6-Substituted methyl penicillins, derivatives and analogues thereof

Disclosed are antibiotic 6-(substituted methyl) penicillins, derivatives and nuclear analogues thereof; wherein the methyl substituent is, inter alia, hydroxyl, ketonic oxygen, imino nitrogen, amino or thio. Also disclosed are processes for the preparatio

Penicillanic acid 1,1-dioxides as β-lactamase inhibitors

Penicillanic acid 1,1-dioxide, and esters thereof readily hydrolyzable in vivo, are useful as antibacterial agents, and also for enhancing the effectiveness of several β-lactam antibiotics against many β-lactamase producing bacteria. Derivatives of penicillanic acid 1,1-dioxide having the carboxy group protected by a conventional penicillin carboxy protecting group are useful intermediates to penicillanic acid 1,1-dioxide. Penicillanic acid 1-oxides and certain esters thereof are useful chemical intermediates to penicillanic acid 1,1-dioxide and its esters.

Derivatives of 6-aminopenicillanic acid

Novel 6-methoxy and 6-thioalkyl-6-acylamidopenicillanic acids and their non-toxic pharmaceutically-acceptable salts, esters and amides which are useful as antibiotics. The products are prepared by treating an ester of 6-substituted-6-aminopenicillanic acid with an acylating agent followed by removal of the ester group. Also disclosed are novel intermediates.