Synthesis and reactivity of 4″-phenylsulfinimine-avermectin B1 and 4′-phenylsulfinimine-avermectin B1 monosaccharide derivative

A short, efficient synthesis of 4″-(R or S)-4″-deoxy-4″-amino-4″-C substituted avermectin B1 and 4′-(R or S)-4′-deoxy-4′-amino-4′-C substituted avermectin B1 monosaccharide 3 and 4 has been developed through the nucleophilic addition of an organometallic reagent to an intermediate phenylsulfinimide 7. These new derivatives of avermectin B1 exhibited potent, broad spectrum insecticidal activity.