Process Chemistry Centre, Laboratory of Wood and Paper Chemistry, Åbo Akademi University, Porthansgatan 3, FIN-20500 Turku, Finland.
Carbohydr Res. 2010 Dec 10;345(18):2610-5. doi: 10.1016/j.carres.2010.09.026. Epub 2010 Sep 27.
The C-6 unit of methyl α-D-galactopyranoside was selectively modified by combining enzymatic oxidation with an indium-mediated allylation reaction. The Barbier-Grignard type reaction, where a carbonyl group reacts with an allyl halide, proceeds in aqueous solution, even with water as the only solvent; thus carbohydrates can be modified without the need for drying or protection-deprotection steps. The corresponding homoallyl alcohols are produced in high yields of >90% in the reactions with allyl bromide and cinnamyl chloride. The main products were isolated and characterized by GC-MS and NMR spectroscopy.
C-6 位的甲基-α-D-吡喃半乳糖苷通过结合酶氧化和铟介导的烯丙基化反应进行选择性修饰。Barbier-Grignard 型反应，其中羰基与烯丙基卤化物反应，在水溶液中进行，甚至可以只用水作为溶剂；因此，碳水化合物可以在不需要干燥或保护-脱保护步骤的情况下进行修饰。与烯丙基溴和肉桂基氯反应时，相应的高烯丙基醇以大于 90%的高产率生成。主要产物通过 GC-MS 和 NMR 光谱进行分离和表征。
