Synthesis of an Oxacepham derivative from 1,2-O-Cyclohexylidene-α-D-Xylofuranose

Abstract

Carbohydrates have gained much attention as cheap chiral starting materials in stereocontrolled target oriented synthesis. β-lactam antibiotics still remain the main tool against bacterial infections but the search for new active compounds has not been the aim of reported investigations. Synthesis of β-lactam antibiotics from carbohydrate precursors played a special role owing to the importance of these classes of compounds in modern chemotherapy. In this report, we carried out this subject to synthesize β-lactam derivative (oxacepham) via [2 + 2] cycloaddition of chlorosulfonyl isocyanate (CSI) to vinyl ether derived from carbohydrate (α-D-glucose).