Synthesis of Acyclic Unsaturated Sugar Derivatives.

Abstract Starting from the new (2E)-4,5,6,7-tetra-O-acetyl-2,3-dideoxy-aidehydo-D-arabino-hept-2-enose (2), or the previously described (2E)-4, 5, 6-tri-O-acetyl-2,3-dideoxy-aldehydo-D-erythro-hex-2-enose (4), a series of acyclic unsaturated sugar derivatives have been synthetized. Compounds 2 and 4 reacted with DBU, leading to 9:1 (2E,4Z)- and (2E,4E)-4-acetoxydienal mixtures. The unsaturated aldimines 10–12 were obtained by reaction of 4 or the dienals 8+9 with primary amines. Selective reduction of aldimines afforded their corresponding allylamines.