74288-40-7Relevant articles and documents
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.
METHOD OF PREPARING INTERMEDIATES OF PENEM ANTIBIOTICS
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Page/Page column 28; 30, (2009/06/27)
The present invention relates to a method of preparing bicyclic keto esters, which are intermediates for carbapenem-based antibiotics. The method of preparing carbapenem-based antibiotic intermediates according to the present invention has not only the fast reaction rate using co-catalysts and specific reaction solvents which may be allowed to have high activity of rhodium catalysts, but also reduces the amount of expensive rhodium catalysts. Therefore, the present invention is very economical and useful, in industrial aspects.
PROCESS FOR PREPARATION OF ESTERS OF 2-DIAZO-3-TRIMETHYLSILYLOXY-3-BUTENOIC ACID
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Page/Page column 13, (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.
Synthesis and biological activities of an α-methyl and a β-methyl carbapenem and the corresponding unsubstituted compound
Pfaendler, Hans Rudolf,Weishaupt, Ralf,Meffert, Helmut
, p. 1389 - 1391 (2007/10/03)
The carbapenem potassium salts 4, 7 and 8 were prepared. Their rates of β-lactam hydrolysis and their biological activities, particularly their β-lactamase inhibiting properties, were examined and explained on the basis of their different substitution and pyramidality. (C) 2000 Elsevier Science Ltd. All rights reserved.
Simple and Condensed β-Lactams. Part 9. Elaboration of the 3-(1-Hydroxyethyl) Side Chains of Potential Intermediates of Carbapenem Antibiotics via the 2-Methyl-1,3-dioxolan-2-yl Group
Fetter, Jozsef,Lempert, Karoly,Kajtar-Peredy, Maria,Simig, Gyula
, p. 1135 - 1142 (2007/10/02)
Deketalization of the trans compounds methyl and ethyl (2RS,3RS)-1-(2,4-dimethoxybenzyl)-3-(2-methyl-1,3-dioxolan-2-yl)-4-oxoazetidine-2-carboxylates 5b and 5c, and of the cis isomer (6b) of the latter leads to 85:15 mixtures of the trans- and cis-compounds methyl (2RS,3RS)- and (2RS,3SR)-3-acetyl-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate (7a) and (8a), respectively of the corresponding ethyl esters (7b) and (8b).Sodium borohydride reduction of the mixture of the trans- and cis-esters (7b) and (8b) gives a mixture of the 1'-epimeric trans-compounds ethyl(2RS,3RS)-1-(2,4-dimethoxybenzyl)-3--4-oxazetidine-2-carboxylate (9b) and (10b).Similar mixtures of 1'-epimeric compounds of the types (9) and (10), carrying a variety of substituents attached to position 2 of their azetidine rings were obtained by successive deketalization and reduction of the corresponding trans-(5) and cis-(6) compounds or their mixtures, as well as by other methods.Ring closure of a mixture of the pair of the 1'-epimeric trans-compounds p-nitrobenzyl 2-diazo-4--4-oxo-azetidin-2-yl>-3-oxobutanoates (9n) and (10n) gave a mixture of the 1'-epimeric compounds p-nitrobenzyl 6--2,7-dioxo-(3RS,5RS,6SR)-carbapenam-3-carboxylates (11) and (12) which was converted into a mixture (13) of the 1'-epimeric bis-protected thienamycin analogues p-nitrobenzyl 2-(2-formylaminoethylthio)-6--7-oxo-(5RS,6SR)-carbapen-2-em-3-carboxylates.
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.
3-[1-Hydroxyethyl]-4-carboxymethyl-azetidin-2-one
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, (2008/06/13)
In a process for the total synthesis of thienamycin from L-aspartic acid via intermediate III: STR1 there is disclosed a process for preparing III via STR2 wherein R is a protecting group.
Process for the preparation of (2S)-tetrahydro-2α-methyl-6-oxo-4βα-carboxylic acid
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, (2008/06/13)
Disclosed is a process for preparing (2S)-tetrahydro-2α-methyl-6-oxo-4β-amino-2H-pyran-3α-carboxylic acid (I) which is useful in the synthesis of thienamycin. The process proceeds via a stereospecific reduction of the 2-acetyl-3-(R)-α-methylbenzylamino-2-pentenedioic acid diester (II). STR1 wherein R is, α-methylbenzyl, and R1 is lower alkyl having 1-6 carbon atoms or arylalkyl such as benzyl.
Process for the preparation of 1-carbapenems and intermediates via trithioorthoacetates
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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 intermediates II and III: STR1 wherein R is hydrogen, a pharmaceutically acceptable ester moiety or salt cation, or a readily removable blocking group; R6 and R7 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl; R1' is hydrogen or a protecting group; and Ra, Rb and Rc are independently selected from alkyl, aryl and aralkyl.
Process for the preparation of thienamycin and intermediates
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, (2008/06/13)
Disclosed is a process for the total synthesis of thienamycin from 4-allylazetidinone (IIIa) via STR1 L-aspartic acid (III): STR2 R=H, blocking group or salt cation.
