The synthesis of oleandrose, the key carbohydrate of the avermectins, and its elaboration to the avermectin disaccharide are described. The three contiguous asymmetric centers of oleandrose are introduced by the reaction of a -methoxyallyl boronate with (S)-2-(benzyloxy)propanol to give a 8.7:1.2:1.0 mixture of diastereomers, the major of which has the oleandrose stereochemistry. The disaccharide was prepared by coupling of l-S-(2-
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