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Short Paper | Regular issue | Vol 91, No. 4, 2015, pp.849-861
Published online, 4th March, 2015
DOI: 10.3987/COM-15-13174
IBr-Catalyzed O-Glycosylation of D-Glucals: Facile Synthesis of 2,3-Unsaturated-O-glycosides

Rungnapha Saeeng, Onanong Siripru, and Uthaiwan Sirion*

*Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Burapha University, Sangsook, Chonburi 20131, Thailand


Iodine monobromide (IBr) is explored as an alternative catalyst for the selective synthesis of 2,3-unsaturated glycosides from tri-O-acetyl-D-glucal 1 with several alcohols through Ferrier rearrangement. This reaction was shown to be a simple, efficient and cost-effective method, affords twenty examples of corresponding glycoside products in high yields with good α-selectivity.