L-グロン酸誘導体の研究(第1報) : Mono-およびDi-O-benzylidene-L-gulonolactoneの構造

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書誌事項

タイトル別名
  • Studies on L-Gulonic Acid Derivatives. I : Structures of Mono- and Di-O-benzylidene-L-gulonolactone.
  • L-グロン酸誘導体の研究-1-Mono-およびDi-O-benzylidene-L-gulonolactoneの構造
  • L-グロンサン ユウドウタイ ノ ケンキュウ 1 Mono- オヨビ Di-O-benzylidene-L-gulonolactone ノ コウゾウ

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L-Gulonolactone (I) was condensed with benzaldehyde to afford mono- and di-O-benzylidene-L-gulonolactone. Mono-O-benzylidene-L-gulonolactone (II) was not oxidized by periodic acid, while its amide was oxidized extremely slowly by periodic acid. II was reduced by sodium borohydride to yield 2, 4-O-benzylidene-D-sorbitol. Therefore, the structure of II was established as 3, 5-O-benzylidene-L-gulonolactone. Di-O-benzylidene-L-gulonolactone (III) was partially hydrolyzed by acid to II. III did not react with ammonia in methanol and was recovered from the reaction mixture. Based on the result of acid hydrolysis of III and from the conformational consideration, it was concluded that III is 2, 6 : 3, 5-di-O-benzylidene-L-gulonolactone.

収録刊行物

  • 薬学雑誌

    薬学雑誌 86 (2), 110-113, 1966

    公益社団法人 日本薬学会

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