101629-27-0Relevant academic research and scientific papers
THE STRUCTURE AND PROPERTIES OF THE PRODUCTS OF REACTION BETWEEN 3,4,6-TRI-O-ACETYL-2-DEOXY-2-NITROSO-α-D-GLUCOPYRANOSYL CHLORIDE AND PYRAZOLE
Smiatacz, Zygfryd,Szweda, Roman,Drewniak, Jolanta
, p. 151 - 160 (2007/10/02)
Dimeric 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-α-D-glucopyranosyl chloride reacts with pyrazole in acetonitrile to give 1-(3,4,6-tri-O-acetyl-2-deoxy-2-hydroxyimino-D-hexopyranosyl)pyrazoles.The reaction is not stereospecific and the products have the α- and β-D-arabino and α- and β-D-ribo structures, with the α-D-arabino and β-D-ribo isomers being the major products. 1-(3,4,6-Tri-O-acetyl-2-deoxy-2-hydroxyimino-α-D-arabino- and -β-D-ribo-hexopyranosyl)pyrazoles have been modified at C-2 and C-3 to afford the following derivatives: 1-(α-D-gluco-, α-D-manno-, 2-acetamido-2-deoxy-α-D-gluco-, and 2-acetamido-2-deoxy-β-D-altro-pyranosyl)pyrazole, 1-(3-azido-2,3-dideoxy-2-hydroxyimino-α- and -β-D-arabino-, and -α- and -β-D-ribo-hexopyranosyl)pyrazole, as well as (Z)- and (E)-1-(2,3-dideoxy-2-hydroxyimino-α-D-glycero-hexopyranosyl)pyrazoles.
