Vorbrüggen Base Introduction Reaction

Vorbrüggen Base Introduction Reaction

The Vorbrüggen method is perhaps the most important method for linking the base to the sugar in the synthesis of nucleosides. It is named after Helmut Vorbrüggen, an industrial chemist at Schering, Berlin, who worked meticulously on optimizing the reaction conditions, building on a substantial body of work in the earlier literature. The method uses a peracylated glycosyl donor, a silylated base, and a mild Lewis acid, typically in the form of a trimethylsilyl cation as active species.

References

[1] H. Vorbrüggen, K. Krolikiewicz, B. Bennua, Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts. Chem. Ber. 1981, 114, 1234-1255. https://doi.org/10.1002/cber.19811140404

[2] H. Vorbrüggen, B. Bennua, A new simplified nucleoside synthesis. Chem. Ber. 1981, 114, 1279-1286. https://doi.org/10.1002/cber.19811140407

[3] B. Bennua-Skalmowski, K. Krolikiewicz, H. Vorbrüggen, A new simple nucleoside synthesis. Tetrahedron Lett. 1995, 36, 7845-7848. https://doi.org/10.1016/0040-4039(95)01667-7