Allosteric Activation of Protein Phosphatase 2C by d-chiro-Inositol-Galactosamine, a Putative Mediator Mimetic of Insulin Action, by

Synthesis of C-Glycoinositols from C-Glycosylcrotylstannanes

“…The fractions containing the desired compounds were collected and the volatiles were removed by SpeedVac. The resultant solution was lyophilized to give 16 (1.9 mg, 46%): R f 0.15 [pyridine/2-propanol/H 2 O/HOAc (8:8:4:1); visualized with the standard TLC stain or ninhydrin]; 7 1 H NMR (600 MHz, D 2 O, external standard: C 6 H 6 ) δ 4.02 (t, J = 3.6 Hz, 1H, H1), 3.97 (t, J = 3.6 Hz, 1H, H6), 3.89 (d, J = 3.2 Hz, 1H, H4′), 3.85 (dd, J = 3.0, 10.5 Hz, 1H, H5), 3.80−3.68 (m, 3H, H2, 5′, 6′), 3.65 (m, 1H, H6′), 3.45 (m, 2H, H3, 3′), 3.46 (bt, J = 9.2 Hz, 1H, H1′), 2.78 (t, J = 10.0 Hz, 1H, H2′), 2.09 (m, 1H, Ha), 1.97 (m, 1H, H4), 1.88 (m, 1H, Ha); 13 Synthesis of β-C-Galactosamino Cyclohexene (17). A solution of 13 (55 mg, 0.058 mmol) in CH 2 Cl 2 (10 mL) was subjected to the RCM procedure described for the synthesis of 14.…”