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光诱导醛糖内酯的电子转移α-脱氧反应。2-脱氧-D-阿拉伯己糖-1,4-内酯的高效合成。

Photoinduced electron-transfer alpha-deoxygenation of aldonolactones. Efficient synthesis of 2-deoxy-D-arabino-hexono-1,4-lactone.

作者信息

Bordoni Andrea, de Lederkremer Rosa M, Marino Carla

机构信息

CIHIDECAR (CONICET), Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina.

出版信息

Carbohydr Res. 2006 Aug 14;341(11):1788-95. doi: 10.1016/j.carres.2006.04.012. Epub 2006 May 11.

Abstract

A photoinduced electron-transfer (PET) reaction was used for the deoxygenation at C-2 of aldonolactones derivatized as 2-O-[3-(trifluoromethyl)benzoyl] or benzoyl esters. By irradiation of different D-galactono- and D-glucono-1,4-derivatives, with a 450W lamp, using 9-methylcarbazole as photosensitizer, the corresponding 2-deoxy-D-lyxo- and 2-deoxy-D-arabino-hexono-1,4-lactones were efficiently obtained.

摘要

光诱导电子转移(PET)反应被用于对衍生为2-O-[3-(三氟甲基)苯甲酰基]酯或苯甲酰酯的醛糖内酯的C-2位进行脱氧反应。通过用450W灯照射不同的D-半乳糖-1,4-衍生物和D-葡萄糖-1,4-衍生物,以9-甲基咔唑作为光敏剂,有效地得到了相应的2-脱氧-D-来苏糖-1,4-内酯和2-脱氧-D-阿拉伯糖-己糖-1,4-内酯。

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