Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
Department of Laboratory Medicine, The Second Affiliated Hospital of Zhejiang University School of Medicine, Hangzhou, 31009, China.
Carbohydr Res. 2020 Sep;495:108074. doi: 10.1016/j.carres.2020.108074. Epub 2020 Jul 12.
Regioselective acetylation of per-O-TMS carbohydrates was achieved preferentially at the 6 position or 1,6-position under mild conditions involving the eco-friendly solvent acetonitrile, at room temperature, in ambient atmosphere and in a shorter time. Good or moderate yields were obtained via 4-dimethylaminopyridine, without auxiliary equipment. A single α-O-Acetyl acetylation anomer was exclusively defined for the involved substrates. A 6-O-monoacetate derivative was applied and used as a stable glycosyl donor in the disaccharides construction. The methodology was successful for a range of substrates, which include the following: d-lactose, d-trehalose, d-galactose, methyl α-d-galactose, d-glucose, d-mannose, d-xylose, and l-fucose.
在温和的条件下，使用环保溶剂乙腈，在室温、环境气氛下并在更短的时间内，可优先实现对全-O-TMS 碳水化合物的区域选择性乙酰化，在 4-二甲氨基吡啶存在下，无需辅助设备，即可获得良好或中等产率。所涉及的底物均被唯一地定义为单 α-O-乙酰化差向异构体。6-O-单酯衍生物被用作稳定的糖基供体，用于二糖的构建。该方法适用于一系列的底物，包括：D-乳糖、D-海藻糖、D-半乳糖、甲基-α-D-半乳糖、D-葡萄糖、D-甘露糖、D-木糖和 L-岩藻糖。
