AN EFFECTIVE STRATEGY FOR THE SYNTHESIS OF O-(2-AMINO-2-DEOXY-ALPHA-D-GLUCOPYRANOSYL)-D-CHIRO AND D-MYO-INOSITOL 1-PHOSPHATE RELATED TO PUTATIVE INSULIN MIMETICS

Two glycosylinositol phosphates related to putative insulin mimetics, o-2-deoxy-alpha-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and ino-2-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), h ave been synthesized from selectively protected and enantiomerically p ure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit w as prepared in a multigram scale from D-glucose using the Ferrier's ca rbocyclization route, and it was transformed into the corresponding my o epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inosit ol derivatives.