74288-39-4Relevant academic research and scientific papers
Atypical Carbapenem Antibiotics with Improved Activity Against Carbapenemase-Producing Acinetobacter baumannii
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, (2020/11/30)
The following invention deals with the design, preparation, evaluation, and use of carbapenem antibiotics with improved activity, relative to current commercially available carbapenem antibiotics, against infections involving multidrug resistant, carbapen
A catalytic asymmetric route to carbapenems
Bodner, Micah J.,Phelan, Ryan M.,Townsend, Craig A.
, p. 3606 - 3609 (2011/03/17)
Image Presented Efficient syntheses of N-acetyl thienamycin and epithienamycin A in their readily deprotected form are reported where three contiguous stereocenters are established in a single catalytic asymmetric azetidinone-forming reaction. These examples are a template for synthesizing C-5/C-6 cis or trans carbapenems with independent control of the C-8 stereocenter. A library of oxidatively and sterochemically defined azetidinone precursors to a variety of naturally occurring carbapenems and potential biosynthetic intermediates has been prepared to facilitate studies of carbapenem antibiotic biosynthesis.
Efficient method for silylation of p-nitrobenzyl-2-diazoacetoacetate
Tewari, Neera,Rai, Bishwa Prakash,Nizar, Hashim,Singh, Shailendra Kumar
, p. 211 - 214 (2007/10/03)
An efficient new method for the silylation of p-nitrobenzyl-2- diazoacetoacetate using hexamethyl disilane and iodine is presented. Copyright Taylor & Francis LLC.
PROCESS FOR PREPARATION OF ESTERS OF 2-DIAZO-3-TRIMETHYLSILYLOXY-3-BUTENOIC ACID
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Page/Page column 12, (2008/06/13)
The present invention relates to a process for the preparation of esters of 2-diazo-3-trimethylsilyloxy-3-butenoic acid which comprises reacting a diazoacetoacetate with iodotrimethylsilane in the presence of an organic base, wherein iodotrimethylsilane is prepared by reacting hexamethyldisilane with iodine. The present invention further relates to converting such esters of 2-diazo-3-trimethylsilyloxy-3-butenoic acid to other compounds, such as a substituted diazoazetidinone, an azetidinone, or a bicyclo ketoester.
Stereoselective reactions. XX. Synthetic studies on optically active β-lactams. III. Stereocontrolled synthesis of chiral intermediate to (+)-thienamycin from D-glucose
Ikota,Yoshino,Koga
, p. 2201 - 2206 (2007/10/02)
A chiral key intermediate (19a) for the synthesis of (+)-thienamycin was synthesized starting from D-glucose. The enol ether 13, obtained from the ketone 11 by Horner-Wittig reaction, was transformed to the corresponding methyl ester 16 by pyridinium chlorochromate oxidation or by employing the Wacker process. The ester 16 was further converted to the β-lactam 19a, which is a useful chiral precursor to (+)-thienamycin.
Carbapenem intermediates
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, (2008/06/13)
A new process is provided for preparing the key carbapenem intermediates of the formula STR1 wherein R5 and R6 each independently represent hydrogen or methyl and R1 represents a conventional carboxyl-protecting group.
Process for the preparation of 1-carbapenems and intermediates via silyl-substituted dithioacetals
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, (2008/06/13)
Disclosed is a process for the total synthesis of 1-carbapenem antibiotics (I) from L-aspartic acid via central intermediates II and III: STR1 wherein R is hydrogen, a pharmaceutically acceptable ester moiety or salt cation, or a readily removable blocking group; R6, R7 and R8 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl; R1' and Re are hydrogen, or a readily removable protecting group; Ra, Rb and Rc are selected from alkyl, aryl or aralkyl.
FROM PENICILLIN TO PENEM AND CARBAPENEM. SYNTHESIS OF 2-OXOCARBAPENAM DERIVATIVE
Hirai, Koichi,Iwano, Yuji,Fujimoto, Katsumi
, p. 3251 - 3254 (2007/10/02)
Previously obtained 4-iodomethylazetidinone derivative (2a) is transformed via the trans-iodopropenylation method into the β-keto ester (8), which is thought to be an important precursor for the synthesis of the carbapenem derivatives.
