title: (S)-Camphorsulfonic acid catalyzed highly stereoselective synthesis of pseudoglycosides.
abstract: A mild and efficient synthesis of pseudoglycosides has been developed using metal free (S)-camphorsulfonic acid. (S)-CSA acts as an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated O-glycosides. A wide range of biologically active natural products, alcohols and thiols could be coupled with glucal to give the desired pseudoglycosides in good to excellent yields with exclusive alpha-stereoselectivity.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore.
authors.forename: Bala Kishan
authors.initials: BK
authors.lastname: Gorityala
authors.forename: Shuting
authors.initials: S
authors.lastname: Cai
authors.forename: Jimei
authors.initials: J
authors.lastname: Ma
authors.forename: Xue-Wei
authors.initials: XW
authors.lastname: Liu
mesh_terms: D002164:Camphor / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D002164:Camphor; C006881:10-camphorsulfonic acid