Synthesis of rapamycin glycoconjugates via a CuAAC-based approach
The conversion of the C40 secondary hydroxyl group of rapamycin into the azido group was followed by copper catalyzed cycloaddition of the resulting azido-rapamcin with various unprotected propargyl O- and S-glycosides and a C-ethynyl derivative. This approach furnished a collection of triazole-brid...
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| Veröffentlicht in: | Tetrahedron letters 2013-12, Vol.54 (51), p.6999-7003 |
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| creator | Moni, Lisa Marra, Alberto Skotnicki, Jerauld S. Koehn, Frank E. Abou-Gharbia, Magid Dondoni, Alessandro |
| description | The conversion of the C40 secondary hydroxyl group of rapamycin into the azido group was followed by copper catalyzed cycloaddition of the resulting azido-rapamcin with various unprotected propargyl O- and S-glycosides and a C-ethynyl derivative. This approach furnished a collection of triazole-bridged rapamycin glycoconjugates (14 examples) in 44–83% isolated yield. |
| doi_str_mv | 10.1016/j.tetlet.2013.10.026 |
| format | Article |
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| ispartof | Tetrahedron letters, 2013-12, Vol.54 (51), p.6999-7003 |
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| language | eng |
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| source | Access via ScienceDirect (Elsevier) |
| subjects | Azido-rapamycin Chemical Sciences Collection Conversion Copper Cycloaddition Derivatives Hydroxyl groups Rapamycin Sugar alkyne Synthesis (chemistry) Tetrahedrons Triazole |
| title | Synthesis of rapamycin glycoconjugates via a CuAAC-based approach |
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