NIS/TMSOTf-Promoted Glycosidation of Glycosyl ortho-Hexynylbenzoates for Versatile Synthesis of O-Glycosides and Nucleosides
| Autor: | Rongkun Liu, Qingting Hua, Qixin Lou, You Yang, Jiazhe Wang, Zhi Ma, Xiaona Li |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Reaction conditions
chemistry.chemical_classification Trimethylsilyl 010405 organic chemistry Chemistry Organic Chemistry Leaving group Glycoside 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Glycosyl Trifluoromethanesulfonate |
| Zdroj: | The Journal of Organic Chemistry. 86:4763-4778 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.1c00151 |
| Popis: | Glycosidation plays a pivotal role in the synthesis of O-glycosides and nucleosides that mediate a diverse range of biological processes. However, efficient glycosidation approach for the synthesis of both O-glycosides and nucleosides remains challenging in terms of glycosidation yields, mild reaction conditions, readily available glycosyl donors, and cheap promoters. Here, we report a versatile N-iodosuccinimide/trimethylsilyl triflate (NIS/TMSOTf)-promoted glycosidation approach with glycosyl ortho-hexynylbenzoates as donors for the highly efficient synthesis of O-glycosides and nucleosides. The glycosidation approach highlights the merits of mild reaction conditions, cheap promoters, extremely wide substrate scope, and good to excellent yields. Notably, the glycosidation approach performs very well in the construction of a series of challenging O- and N-glycosidic linkages. The glycosidation approach is then applied to the efficient synthesis of oligosaccharides via the one-pot strategy and the stepwise strategy. On the basis of the isolation and characterization of the departure species derived from the leaving group, a plausible mechanism of NIS/TMSOTf-promoted glycosidation of glycosyl ortho-hexynylbenzoates is proposed. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|