105344-46-5Relevant articles and documents
Practical synthesis of 1β-methylcarbapenem antibiotics: Side-chain substitution reaction of 2-arylsulfinyl and 2-arylsulfonyl carbapenems
Oda, Kozo,Yoshida, Akira
, p. 893 - 899 (2007/10/03)
The C-2 side-chain substitution reaction of a sulfoxide and a sulfone derived from a p-nitrobenzyl (1R,5S,6S)-6-[(1R)-1-(tert- butyldimethylsilyloxy)ethyl]-2-[2-(diethylcarbamoyl)phenylthio]-1- methylcarbapen-2-em-3-carboxylate with various mercaptans progressed smoothly in the presence of magnesium bromide. Bromomagnesium thiolate prepared from mercaptans proved to be especially effective for the substitution reaction and gave precursors of 1β-methylcarbapenem antibiotics in high yield.
Synthetic studies of carbapenem and penem antibiotics. V. Efficient synthesis of the 1β-methylcarbapenem skeleton
Sunagawa,Sasaki,Matsumura,Goda,Tamoto
, p. 1381 - 1387 (2007/10/02)
An efficient synthesis of 1β-methylcarbapenem from the 1-(2- oxoazetidinyl)acetate 8 was developed by application of the Dieckmann reaction. Dieckmann-type cyclization of 8 and conversion to the enolphosphate 10 were achieved without epimerization to the 1α-methyl isomer in a one-pot procedure. Treatment with the mercaptan 22 after the phosphorylation resulted in a practical one-pot preparation of the 1β-methylcarbapenem derivative 23 from 8.