Highly Effective Resolution of 1,3-Dibenzyl-6-hydroxy-3,3a, 6,6a-tetrahydro-1H-furo[3,4-d]imidazole-2,4-dione, an Intermediate for Biotin, with Optically Active Amines and Reutilizatin of the Unwanted Epimer

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概要

• 論文の詳細を見る

• The direct resolution of (3aRS, 6SR, 6aSR)-1,3-dibenzyl-6-hydroxy-3,3a, 6,6a-tetrahydro-1H-furo[3,4-d]imidazole-2,4-dione [(±)-9], a key intermediate for biotin, with optically active amines was examined. Reaction of (±)-9 with cinchonidine readili gave the cinchonidine salt of the (4S, 5R)-aldehyde-carboxylic acid (12), acidification of which gave (3aS.6R, 6aR)-9,convertible to biothin. N-alkyl-D-glucamines (14) were also found to be effective resolving agents for (±)-9 applicable for industrial use. Reutilizatin of the unwanted epimer [(3aR, 6S, 6aS)-9] was effected by facile oxidation to the meso-diacid (3) with sodium chlorite.

• 公益社団法人日本薬学会の論文
• 1990-04-25

著者

• 岡村 公生

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 伊達 忠正

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 瀬沼 勝

  Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.,

• 岡村 公生

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 絹巻 明生

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 伊達 忠正

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 藤井 武彦

  Osaka Factory, Tanabe Seiyaku Co., Ltd.,

• 瀬戸 正彦

  Osaka Factory, Tanabe Seiyaku Co., Ltd.,

• 瀬沼 勝

  Research Laboratory Of Applied Biochemistry

• 瀬戸 正彦

  Osaka Factory Tanabe Seiyaku Co. Ltd.

• 藤井 武彦

  Osaka Factory Tanabe Seiyaku Co. Ltd.

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