Photochemical conversion of the o-nitrobenzyl-C-glucoside to a sugar lactone |
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Authors: | Kohri Michinari Kimura Takuma Shinoda Yoshihiro Taniguchi Tatsuo Nakahira Takayuki |
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Institution: | Division of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Chiba 263-8522, Japan. kohri@faculty.chiba-u.jp |
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Abstract: | A new family of activated glycosidic compounds has been designed and synthesized: (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-nitrophenylmethane (1). It is stable in conditions commonly used for synthesis, and it can be converted to a sugar lactone derivative merely by photoirradiation (λ=365 nm): 2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone (2). A mechanism for the reaction is proposed. The photochemical conversion of 1 in the presence of methanol has also been demonstrated, giving rise to methyl 2,3,4,6-tetra-O-acetyl-D-gluconate (3). |
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