Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA 70803, United States.
Carbohydr Res. 2013 Mar 22;369:42-7. doi: 10.1016/j.carres.2013.01.004. Epub 2013 Jan 16.
Exceptionally mild procedures for the visible light photocatalytic activation of selenoglycoside donors in the presence of alcohol acceptors have been developed. This process is demonstrated with both 1-phenylselenyl-2,3,4,6-tetra-O-benzyl glucoside (1) and 1-phenylselenyl-2,3,4,6-tetra-O-benzyl galactoside (2). Catalysis is effected with both metal (Ru(bpy)3) and organocatalysts (diphenyldiselenide). Reactions afford, in all cases, primarily the α-anomers with selectivities that vary with solvent. This represents the first example of a visible light-promoted O-glycosylation.
已经开发出了在醇受体存在下通过可见光光催化激活硒糖苷供体的非常温和的方法。该过程使用 1-苯硒基-2,3,4,6-四-O-苄基葡萄糖苷（1）和 1-苯硒基-2,3,4,6-四-O-苄基半乳糖苷（2）进行了证明。金属（Ru(bpy)3）和有机催化剂（二苯基二硒醚）都可以实现催化。在所有情况下，反应主要生成α-异构体，其选择性随溶剂而变化。这代表了首例可见光促进的 O-糖基化反应。
