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N‑Halosuccinimide/AgNO3‑Efficient Reagent Systems for One-Step Synthesis of 2‑Haloglycals from Glycals: Application in the Synthesis of 2C-Branched Sugars via Heck Coupling Reactions

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journal contribution
posted on 21.02.2014, 00:00 by Suresh Dharuman, Yashwant D. Vankar
An expedient one-step synthesis of 2-iodoglycals and 2-bromoglycals from glycals using NIS/AgNO3 and NBS/AgNO3 as reagent systems has been developed. The utility of these 2-haloglycals has been demonstrated by converting them into 2C-branched glycals via the Heck coupling reaction. Ferrier reaction of tri-O-acetyl-2-iodoglycals followed by Heck coupling reaction with methyl acrylate leads to 2C-branched O-glycosides.