Iminosugar C-Nitromethyl Glycosides and Divergent Synthesis of Bicyclic Iminosugars
| Autor: | Soundararasu Senthilkumar, Sundarababu Baskaran, Akriti Srivastava, Sure Siva Prasad |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Bicyclic molecule 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Iminosugar Intramolecular cyclization Glycoside 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Cascade reaction Stereoselectivity Physical and Theoretical Chemistry Divergent synthesis |
| Zdroj: | Organic Letters. 19:4403-4406 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | An efficient one-pot method for the stereoselective synthesis of novel iminosugar C-nitromethyl glycosides is described. This new class of iminosugar glycosides has versatile nitromethyl functionality whose utility was further demonstrated in the single-step synthesis of bicyclic iminosugars. Under reagent-free conditions, the N-allyl-C-nitromethyl glycosides resulted in intramolecular cyclization to iminosugar-oximes, whereas under SET oxidation, they furnished cyclopropane-fused iminosugars. The N-propargyl-C-nitromethyl glycosides underwent an unprecedented ketenimine-acrylamidine-Michael addition cascade reaction to give bicyclic amidines. |
| Databáze: | OpenAIRE |
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