(S)-Camphorsulfonic acid catalyzed highly stereoselective synthesis of pseudoglycosides.
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.
Gorityala
Bala Kishan
BK
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore.
Cai
Shuting
S
Ma
Jimei
J
Liu
Xue-Wei
XW
D002164:Camphor / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D006027:Glycosides; D002164:Camphor; C006881:10-camphorsulfonic acid