A Practical and Stereocontrolled Synthesis of a Versatile 1β-Methylcarbapenem Intermediate

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概要

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• 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.

• 公益社団法人日本薬学会の論文
• 1997-09-15

著者

• Oda Kozo

  Medicinal Chemistry Research Laboratories Sankyo Co. Ltd.

• YOSHIDA Akira

  Medicinal Chemistry Research Laboratories, Sankyo Co., Ltd.,

• Yoshida Akira

  Medicinal Chemistry Research Laboratories Sankyo Co. Ltd.

関連論文

• Practical Synthesis of 1β-Methylcarbapenem Antibiotics : Side-Chain Substitution Reaction of 2-Arylsulfinyl and 2-Arylsulfonyl Carbapenems
• A Practical and Stereocontrolled Synthesis of a Versatile 1β-Methylcarbapenem Intermediate

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