An Effective Strategy for the Synthesis of 6-O-(2-Amino-2-deoxy-.alpha.-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-Phosphate Related to Putative Insulin Mimetics

Abstract

Two glycosylinositol phosphates related to putative insulin mimetics, 6-0-(2-amino-2-deoxy-alfa-D- glucopyranosyl)-D-chiro-inositol 1-phosphate and 6-0-(2-amino-2-deoxy-alfa-D-glucopyranosyl)-D- myo-inositol 1-phosphate , have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.