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.
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.
Department of Chemistry, Indian Institute of Technology , Kanpur 208 016, India.
Suresh
S
Dharuman
Yashwant D
YD
Vankar
D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D012835:Silver Nitrate / Q000737:chemistry; D013237:Stereoisomerism; D013388:Succinimides / Q000737:chemistry
D006027:Glycosides; D006842:Hydrocarbons, Brominated; D006847:Hydrocarbons, Iodinated; D007202:Indicators and Reagents; D013388:Succinimides; D012835:Silver Nitrate