1448356-41-9Relevant academic research and scientific papers
Synthesis of branched iminosugars through a hypervalent iodine(III)-mediated radical-polar crossover reaction
Santana, Andres G.,Paz, Nieves R.,Francisco, Cosme G.,Suarez, Ernesto,Gonzalez, Concepcion C.
, p. 7527 - 7543 (2013/09/02)
The synthesis of a novel type of branched iminosugars is described. This synthetic strategy is based on two key reactions: first, an aldol reaction with formaldehyde in order to introduce selectively the hydroxymethyl branch, and second, a tandem β-fragmentation-intramolecular cyclization reaction. The combination of both reactions afforded a battery of compounds exhibiting a great structural complexity, with the concomitant formation of a quaternary center, starting from readily available aldoses. With this approach we have demonstrated the usefulness of the fragmentation of anomeric alkoxyl radicals (ARF) promoted by the PhIO/I2 system for the preparation of new compounds with potential interest for both medicinal and synthetic chemists.
