Division of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Chiba 263-8522, Japan.
Carbohydr Res. 2011 Dec 27;346(18):2965-9. doi: 10.1016/j.carres.2011.10.027. Epub 2011 Oct 20.
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).
（2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基）-2-硝基苯甲醚（1）。它在常用于合成的条件下稳定，并且仅通过光照射（λ=365nm）就可以转化为糖内酯衍生物：2,3,4,6-四-O-乙酰基-D-葡萄糖-1,5-内酯（2）。提出了一种反应机制。还证明了在甲醇存在下 1 的光化学转化，生成甲基 2,3,4,6-四-O-乙酰基-D-葡萄糖酸酯（3）。
