Synthesis and Structure of 1-D-6-O-(2-Amino-2-deoxy-α- and -β-D-gluco- and -galactopyranosyl)-3-O-methyl-D-chiro-inositol

A convenient preparative synthesis of 1-D-6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-3-O-methyl-chiro-inositol (Ia), 1D-6-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-3-O-methylchiro-inositol (Ib), 1-D-6-O-(2-amino-2-deoxy-α-D-galactopyranosyl)-3-O-methyl-chiro-inositol (IIa), and 1-D-6-O-(2-amino-2-deoxy-β-D-galactopyranosyl)-3-O-methyl-chiro-inositol (IIb) from 3-O-methyl-D-chiro-inositol (pinitol) as starting material is reported. These compounds contain some of the basic structural motifs proposed for insulin mediators. The three-dimensional structures of these compounds have been determined by NMR spectroscopy and molecular dynamics simulations.