101765-69-9Relevant articles and documents
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 (2001)
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.
2-Picolyl thioesters; A useful synthon for the preparation of 1-β-alkyl carbapenem intermediates
Martel,Daris,Bachand,Corbeil,Menard
, p. 1537 - 1539 (2007/10/02)
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Synthetic study of 1-substituted carbapenem antibiotics
Shibata,Iino,Tanaka,et al.
, p. 4739 - 4742 (2007/10/02)
Total synthesis of 1-substituted carbapenems is described. The key step is the reaction of acetoxyazetidinone with ketene silyl acetal.