Glycosidation route to 4"-epi-methylamino-4"-deoxyavermectin B.s

Details Glycosidation route to 4"-epi-methylamino-4"-deoxyavermectin B.s Glycosidation route to 4"-epi-methylamino-4"-deoxyavermectin B.s

1993-09-29

1995-03-21

Tsang, Cecilia

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D49322

Patent

active

053997174

ABSTRACT:
A stereocontrolled glycosidation with thiophenyl 4-(N-allyloxycarbonyl)-epi-methylamino-4-deoxyoleandrose and 5-O-allyloxycarbonyl avermectin B.sub.1 monosaccharide using N-iodosuccinimide produces exclusively the .alpha.-anomer of a precursor of 4"-epi-methylamino-4"-deoxyavermectin B.sub.1 in 90% yield. Deprotection and crystallization as the benzoic acid salt yields 4"-epi-methylamino-4"-deoxyavermectin B.sub.1 (emamectin benzoate), a potent insecticide.

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