Study on the reaction behavior of L-ascorbic acid and phenylboronic acid

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  • L -アスコルビン酸とフェニルボロン酸との反応挙動の評価
  • L-アスコルビンサン ト フェニルボロンサン ト ノ ハンノウ キョドウ ノ ヒョウカ

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Abstract

This study shows reaction behavior of L-ascorbic acid (AA) and phenylboronic acid (PB) in DMSO-d6 (50 mM at 30oC) to form the corresponding boronic acid ester. For the purpose of restriction of the reactive moieties, two AA derivatives, in which diols at 2,3- or 5,6-position are protected, were selected and evaluated as the reference for AA. Compared among their 1H NMR spectra of the boronic acid ester from the protected AA with PB, unmodified AA was reacted with PB mainly at not the 2,3-position but the 5,6-position of AA. When equimolar AA and PB were mixed in DMSO-d6, it was found that approximately a half of AA was converted to the boronic acid ester.

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