Practical synthesis of 1β-methylcarbapenem antibiotics: Side-chain substitution reaction of 2-arylsulfinyl and 2-arylsulfonyl carbapenems

DOI: 10.1248/cpb.46.893

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 893 - 899 (1998)

Update date:2022-09-26

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Authors:

Oda, Kozo

Yoshida, Akira

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Article abstract of DOI:10.1248/cpb.46.893

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.

Full text of DOI:10.1248/cpb.46.893

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Product name:1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-[(diethylamino)carbonyl]phenyl]sulfinyl]-6-[(1R)-1-[[(1,1-dimethyleth yl)dimethylsilyl]oxy]ethyl]-4-methyl-7-oxo-, (4-nitrophenyl)methyl ester, (4R,5S,6S)-

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