Synthesis of Amino Acid and 4,5-Dihydro-6H-1,3-thiazine Derivatives for the Preparation of Cephalosporin Compounds

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概要

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• Several β-hydroxy-α-halogeno-α-amino acid derivatives (3-5) were prepared from tert-butyl N-benzylideneglycinate (1) and α-haloketones or an α-haloaldehyde for utilization in the synthesis of 4,5-dihydro-6H-1,3-thiazine derivatives (7 and 12). An alternative thiazine synthesis starting from tert-butyl glycinate (13) was found to proceed stereoselectively, giving rise to 12a. The two thiazine derivatives 7 and 12a were converted into cephalosporin derivatives (10 and 17,respectively) by reaction with azidoacetyl chloride. The 7-azido-3-methylcephem derivative (17) was further led to 7-aminodeacetoxycephalosporanic acid (7-ADCA, 22).

• 社団法人日本薬学会の論文
• 1980-10-25

著者

• 宮寺 哲男

  Central Research Laboratories, Sankyo Co., Ltd.

• 田中 輝夫

  Central Research Laboratories, Sankyo Co., Ltd.

• 田中 輝夫

  Central Research Laboratories Sankyo Co. Ltd.

• 渡辺 泰一郎

  Chemical Research Laboratories Sankyo Co. Ltd.

• 橋本 敏彦

  Central Research Laboratories Sankyo Co. Ltd.

• 渡辺 泰一郎

  Central Research Laboratories, Sankyo Co., Ltd.

• 宮寺 哲男

  Chemical Research Laboratories, Sankyo Co., Ltd.

• 橋本 俊彦

  Central Research Laboratories, Sankyo Co., Ltd.

• 川野 洋一

  Central Research Laboratories, Sankyo Co., Ltd.

• 川野 洋一

  Central Research Laboratories Sankyo Co. Ltd.

• 橋本 俊彦

  Central Research Laboratories Sankyo Co. Ltd.

• 宮寺 哲男

  Chemical Research Laboratories Sankyo Co. Ltd.

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