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Paper | Regular issue | Vol 78, No. 10, 2009, pp.2443-2454
Published online, 30th June, 2009
DOI: 10.3987/COM-09-11729
A Facile Iodine-catalyzed Glycosylation: Enantiomerically Pure β-Lactams with the Thienamycin Side Chain

Bimal K. Banik,* Oliwia Zegrocka, Maghar S. Manhas, and Ajay K. Bose

*Department of Chemistry, College of Science and Engineering, The University of Texas-Pan American, 1201 West Univeristy Dr., Edinburg, TX 78539, U.S.A.


A facile iodine-catalyzed glycosylation of the hydroxyethyl side chain as present in thienamycin side chain has been achieved with tri-O-acetyl-D-glucal. This method has produced two separable diasteromeric α-glycosides in excellent yields which on acid-induced cleavage have provided two optically pure alcohols. The absolute stereochemistry of the products has been determined from physiochemical data.