- 著者
- Kozo ODA Akira YOSHIDA
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.46, no.6, pp.893-899, 1998-06-15 (Released:2008-03-31)
- 参考文献数
- 18
- 被引用文献数
- 1 1
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.
1 0 0 0 OA A Practical and Stereocontrolled Synthesis of a Versatile 1β-Methylcarbapenem Intermediate
- 著者
- Kozo ODA Akira YOSHIDA
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.45, no.9, pp.1439-1446, 1997-09-15 (Released:2008-03-31)
- 参考文献数
- 14
- 被引用文献数
- 3 5
S-[2-(Dialkylaminocarbonyl)phenyl](2R)-2-[(3S, 4S)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-oxo-4-azetidinyl]thiopropionate (11), useful intermediates for the synthesis of 1β-methylcarbapenems including 1β-methylthienamycin, were prepared in a highly stereoselective manner by the reaction of E-1-(tert-butyldimethylsilyloxy)-1-[2-(dialkylaminocarbonyl)phenylthio]-1-propene (10) with commerically available (3S, 4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (6) in the presence of zinc chloride catalyst. The diethylaminocarbonyl derivative (11b) was particularly convenient for practical production because of its highly crystalline nature.
- 著者
- KOZO ODA TAKAHIDE NISHI
- 出版者
- JAPAN ANTIBIOTICS RESEARCH ASSOCIATION
- 雑誌
- The Journal of Antibiotics (ISSN:00218820)
- 巻号頁・発行日
- vol.50, no.5, pp.446-448, 1997-05-25 (Released:2006-11-25)
- 参考文献数
- 10
- 被引用文献数
- 2 2