DIASTEREOSELECTIVE ADDITION OF GRIGNARD-REAGENTS TO 3,4-O-ISOPROPYLIDENE-1-O-TRIPHENYLMETHYL-L-GLYCERO-2-TETRULOSE AND 1-O-BENZOYL-3,4-O-ISOPROPYLIDENE-L-GLYCERO-2-TETRULOSE

Diastereoselectivity in the addition of Grignard reagents (RMgX) to 3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose (1) and 1-O-benzoyl-3,4-O-isopropylidene-L-glycero-2-tetrulose (2) depended remarkably on R, X, the solvent, and the reaction temperature. In the reaction of 1 in diethyl ether at 0-degrees-C and 2 in tetrahydrofuran were obtained (2R,3S)-adducts with moderate to high diastereoselectivity, while in the reaction of 2 in diethyl ether at-78-degrees-C (2S,3S)-adducts were the major products. (2R)-2-Hydroxymethyl-2-nonyloxirane and (2S)-2-hydroxymethyl-2-tetradecyloxirane were synthesized.