Extremely Mild and Selective Method for Hydrolysis of Tosyl Esters by Photo-Sensitized Single Electron Transfer Reactions

Atsushi NISHIDA; Tatsuo HAMADA; Osamu YONEMITSU

doi:10.1248/cpb.38.2977

Atsushi NISHIDA, Tatsuo HAMADA, Osamu YONEMITSU

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Keywords: tosyl ester, hydrolysis, UV irradiation, photo-sensitization, electron-rich aromatic compound, single electron, transfer, sugar, nucleoside

JOURNAL FREE ACCESS

1990 Volume 38 Issue 11 Pages 2977-2980

DOI https://doi.org/10.1248/cpb.38.2977

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Abstract

Tosyl esters were hydrolyzed by irradiation with ultraviolet light (>330nm) under photo-sensitized conditions. 1.5-Dimethoxynaphthalene and (4, 8-dimethoxynaphthyl)propionic acid were effective for the transformation in aqueous acetonitrile in the presence of hydrazine. The reaction was successfully applied to the hydrolysis of tosylates of sugars and nucleosides.

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