Synthesis of polyprenyl diphosphate sugars and uridine diphosphate sugars – derivatives of N-acetyl-D-quinovosamine and N-acetyl-D-fucosamine
S. D. Maltsev, L. L. Danilov, V. N. Shibaev
N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow
Abstract: 2-Acetamido-2,6-dideoxy-3,4-di-O-acetyl-α-D-glucose and -galactose phosphates were synthesized from the corresponding Li-alkoxides and tetrabenzyl diphosphate followed by hydrogenolysis. The acetylated phosphates were converted into moraprenyl diphosphate sugars by the reaction with moraprenyl phosphoroimidazolidate followed by O-deacylation, and into uridine diphosphate sugars through interaction with uridine-5'-diphenyldiiphosphate followed by O-deacetylation.
Russian Journal of Bioorganic Chemistry 1991, 17 (4):540-545