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

Azobenzene-Avermectin B1a Derivatives for Optical Modulation of Insect Behaviors

“…Avermectins have been widely used as pest control agents because of their demonstrated efficacy and unique modes of action, and many derivatives with improved bioactivities and/or safety have been commercialized . Among previous studies on structure–activity-relationship investigation, the modification at the 4″-position appeared to be the most efficient approach to increase the insecticidal potency. − For example, the commercial analogue emamectin, which has a methylamino group in epi-orientation at the 4″-position, possesses a 1500-fold increase in potency in comparison with avermectin B1 . Though it was believed that the hydroxyl group at the 5-position was essential for high potency and broad-spectrum activity, some 5-acyloxyimino-5-deoxyavermectin B1 derivatives possess better acaricidal/antiparasitic activity .…”

The Art of the Soluble: Synthetic Problems from Industry as a Springboard for the Discovery of New Chemical Reactions

“…Recently, a few very impressive applications of this mild route to N-sulfanylimines were reported. These include the synthesis of the avermectin B1 (mixtures of B1a and B1b) derivatives 72a and 72b in high yield from the corresponding oximes by Jung and co-workers at Syngenta, 21 and the analogous erythromycin derivatives disclosed by Lukin and Narayanan of Abbott and by Vilarrasa and co-workers. 22…”

Insights into the Photodecomposition of Azidomethyl Methyl Sulfide: A S2/S1 Conical Intersection on Nitrene Potential Energy Surfaces Leading to the Formation of S-Methyl-N-sulfenylmethanimine

“…This type of rearrangement represents the least common rearrangement among those pathways described in the literature and can be considered to be Type 3 pathway in the present work (Scheme ). The possible formation of the rearrangement product, according to Type 3 pathway, would be relevant because the obtained N -sulfenylimines ( N -alkylidenesulfenamides) , are useful intermediates in the syntheses of antibiotics and other bioactive molecules. , N -sulfenylimines have a remarkable reactivity, with possible redox processes at the imine bond (i.e., reduction) and sulfur (i.e., oxidation) as well as nucleophilic additions at the same carbon and electrophilic additions at the nitrogen.…”

“…The possible formation of the rearrangement product, according to Type 3 pathway, would be relevant because the obtained N-sulfenylimines (N-alkylidenesulfenamides) 24,25 are useful intermediates in the syntheses of antibiotics and other bioactive molecules. 26,27 N-sulfenylimines have a remarkable reactivity, with possible redox processes at the imine bond (i.e., reduction) and sulfur (i.e., oxidation) as well as nucleophilic additions at the same carbon and electrophilic additions at the nitrogen.…”