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Published on: May 27, 2015
Aglycon reactivity as a guiding principle in latent-active approach to chemical glycosylations
Anupama Das1, Narayanaswamy Jayaraman1
1Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012, India.
Abstract:
Chemical glycosylations critically depend on the activation of a glycosyl donor and the reaction of this activated donor intermediate with an acceptor alcohol. Whereas many strategies are developed for the activation of an anomeric aglycon substituent, the latent-active method of glycosylation is based specifically on tuning the reactivity of the aglycon substituent of a glycosyl donor. Several novel methods have emerged to install reactive aglycon moiety in a glycosyl donor and fine-tuning the reactivity of the moiety. Remote functionalizations of the aglycon plays a key role in the reactivity tuning. Activation of a remote functionality enables an otherwise latent aglycon to an active moiety, suitable as a glycosyl donor. The latent-active approach provides an advantage to avoid the conversion of the aglycon to another donor prior to a glycosylation, in addition to advancing the contemporary glycosylations with alternate insights. The review analyzes the methodologies that consolidate the latent-active approach to chemical glycosylations.
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