(S)-Camphorsulfonic acid catalyzed highly stereoselective synthesis of pseudoglycosides
Bala Kishan Gorityala1, Shuting Cai, Jimei Ma
1Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore.
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.
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