Dehydroxy Substitution Reactions of the Anomeric Hydroxy Groups in Some Protected Sugars Initiated by Anodic Oxidation of Triphenylphosphine
スポンサーリンク
概要
- 論文の詳細を見る
The anodic transformation of 2,3 : 5,6-di-O-isopropylidene-α-D-mannofuranose (4) and 2,3,4,6-tetra-O-benzyl-D-glucopyranose (5) to the corresponding alkoxy phosphonium ions induces dehydroxy substitution of the sugars at the anomeric positions. Their dehydroxy fluorination and chlorination has been achieved by constant-current electrolysis with CH_2Cl_2-1,2-dimethoxyethane/Ph_3P/Ph_3PH・BF_4 and with CH_2Cl_2/Ph_3P/Et_4N・Cl, respectively.The electrolysis in the presence of Ph_3P has proved to serve O-glycosylation with 4 or 5 as a glycosyl donor, provided that an aliphatic alcohol as a glycosyl acceptor is a weaker nucleophile, such as (CF_3)_2CHOH, CF_3CH_2OH, and tert-BuOH, than the protected sugar toward Ph_3P^<+・> generated anodically from Ph_3P. The present electrochemical reactions for 2,3,4,6-tetra-O-acetyl-D-glucopyranose were unsuccessful, except for the dehydroxy chlorination.
- 公益社団法人日本薬学会の論文
- 1998-06-15
著者
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OHMORI Hidenobu
Graduate School of Pharmaceutical Sciences, Osaka University
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MAEDA Hatsuo
Faculty of Pharmaceutical Sciences, Osaka University
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OHMORI Hidenobu
Faculty of Pharmaceutical Sciences, Osaka University
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Koide T
Faculty Of Pharmaceutical Sciences Osaka University
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Koide Takashi
Tokyo Research Laboratories Kowa Co. Ltd.
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Matsumoto Shun-ichiro
Institute For Drug Discovery Research Yamanouchi Pharmaceutical Co. Ltd.
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Maeda Hatsuo
Faculty Of Pharmaceutical Sciences Osaka University
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Matsumoto Sayaka
Faculty Of Pharmaceutical Sciences Osaka University
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Koide Takashi
Faculty Of Pharmaceutical Sciences Osaka University
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Ohmori H
Graduate School Of Pharmaceutical Sciences Osaka University
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Ohmori Hidenobu
Faculty Of Pharmaceutical Sciences Osaka University
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Koshi T
Tokyo Research Laboratories Kowa Co. Ltd.
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