85281-73-8Relevant academic research and scientific papers
β-lactams derived from a carbapenem chiron are selective inhibitors of human fatty acid amide hydrolase versus human monoacylglycerol lipase
Feledziak, Marion,Michaux, Catherine,Urbach, Allan,Labar, Geoffray,Muccioli, Giulio G.,Lambert, Didier M.,Marchand-Brynaert, Jacqueline
supporting information; experimental part, p. 7054 - 7068 (2010/06/17)
A library of 30 β-lactams has been prepared from (3R,4R)-3-[(R)- 1′-(tbutyldimethylsilyloxy)-ethyl]-4-acetoxy-2-azetidinone, and the corresponding deacetoxy derivative, by sequential N- and O-functionalizations with various ω-alkenoyl and ω-arylalkanoyl c
1β-Methylcarbapenem intermediates via the thiolysis of a Meldrum's precursor
Jacopin, Christophe,Laurent, Mathieu,Belmans, Marc,Kemps, Luc,Cérésiat, Marcel,Marchand-Brynaert, Jacqueline
, p. 10383 - 10389 (2007/10/03)
5-{3-[1-(tert-Butyldimethylsilyloxy)ethyl]-4-oxo-azetidin-2-yl}-2,2,5- trimethyl-[1,3]dioxane-4,6-dione (3) has been submitted to nucleophilic attack with various nucleophiles. Meldrum's moiety transesterification, C4-substitution, β-lactam ring opening and Meldrum's moiety decarboxylation were observed. Reaction of 3 with ethanethiol and dimethylaminopyridine in ethanol quantitatively furnished ethyl 2-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxo-azetidin-2-yl}- thiopropionate as the 1:1 mixture of β (7a) and α (8a) diastereoisomers.
An efficient synthesis of 4-heterofunction-substituted 3-(1-hydroxy)ethylazetidin-2-ones from 3-(1-hydroxy)ethyl-4-phenylsulfinylazetidin-2-one by reaction with silylated heteronucleophiles
Kita,Shibata,Yoshida,Tohjo
, p. 1733 - 1736 (2007/10/02)
3-(1-tert-Butyldimethylsiloxy)ethyl-4-sulfinylazetidin-2-one was reacted with silylated N-, S-, O-, and P-nucleophiles in the presence of a catalytic amount of ZnI2 to give the corresponding trans-4-heterofunction-substituted azetidin-2-ones in high yields.
Chemistry of O-Silylated Ketene Acetals: An Efficient Synthesis of Carbapenem and 1β-Methylcarbapenem Intermediates
Kita, Yasuyuki,Shibata, Norio,Tohjo, Takashi,Yoshida, Naoki
, p. 1795 - 1800 (2007/10/02)
3-(1-tert-Butyldimethylsiloxyethyl)-4-phenylsulfinylazetidin-2-one reacted smoothly with various types of O-silylated ketene acetals and silylated enol ethers in the presence of a catalytic amount of zinc iodide to give the corresponding trans-4-substitut
A NOVEL SUBSTITUTION REACTION OF 4-SULFINYLAZETIDIN-2-ONE WITH SILYLATED HETERONUCLEOPHILES: AN EFFICIENT SYNTHESIS OF 4-HETEROFUNCTION SUBSTITUTED 3-(1-HYDROXY)ETHYLAZETIDIN-2-ONES
Kita, Yasuyuki,Shibata, Norio,Yoshida, Naoki,Tohjo, Takashi
, p. 2375 - 2378 (2007/10/02)
4-Sulfinylazetidin-2-one was reacted with silylated heteronucleophiles in the presence of a catalytic amount of zinc iodide to give the corresponding trans-4-heterofunction substituted azetidin-2-ones in high yields.
A Novel Carbon-Carbon Bond Formation Reaction at the C4 Position of an Azetidin-2-one by Means of Radical Cyclization
Kametani, Tetsuji,Chu, Shih-Der,Itoh, Akira,Maeda, Sayuri,Honda, Toshio
, p. 2683 - 2687 (2007/10/02)
A novel synthesis of carbacepham ring systems through 1,6-bond coupling by a radical cyclization reaction is described.
FROM PENICILLIN TO PENEM AND CARBAPENEM. II. SYNTHESIS OF 3,4-DISUBSTITUTED AZETIDINONE DERIVATIVES FROM 6,6-BIS(PHENYLSELENYL)PENICILLANATE
Hirai, Koichi,Iwano, Yuji,Fujimoto, Katsumi
, p. 4021 - 4024 (2007/10/02)
6,6-Bis(phenylselenyl)penicillanate 2a was converted into 6-1'-(R)-hydroxyethyl substituted penicillanate 5 in high yield.Compound 5 was deselenylated to 10.Oxidation, and then the basic epimerization of cis sulfone 11 gave trans sulfone derivative 12.The trans sulfone 12 was degraded to the monocyclic β-lactams 14, 15 which are important precursors for the carbapenem synthesis.
