著者

瀬沼 勝 藤井 武彦 瀬戸 正彦 岡村 公生 伊達 忠正 絹巻 明生

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.38, no.4, pp.882-887, 1990-04-25

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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.