Chemical synthesis of methyl-(1→3)- and -(1→4)-D-ribopyranosyl-β-D-ribopyranosides. (1→3)- and (1→4)-D-ribopyranosides
V. I. Betaneli, A. Ya. Ott, N. K. Kochetkov
N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow
Abstract: By means of the trityl-cyanoethylidene condensation method, anomeric pairs of methyl-D-ribopyranosyl-β-D-ribopyranosides ((1→3)-linked, overal yield 84%, β:α=7.3:1, and (1→4), 84%, β:α=4.3:1), and two D-ribopyrananes ((1→3)-linked, 90% yield, 11% α-linkages, average degree of polymerization 30, and (1→4), 97%, 18%, 27, respectively) have been synthesized starting with D-ribose. No typical correlations between the anomeric carbon atom chemical shifts and the glycosidic centre configuration for the afore mentioned compounds were revealed. Intramolecular cyclisation of 1,2-O-[1-(exo-cyano)ethylidene]-α-D-ribopyranose as well as its 3-trityl ether into 1,2,4-orthoacetyl-α-D-ribopyranose and 1,2,4-orthoacetyl-3-O-triphenylmethyl-α-D-ribopyranose, respectively, have been observed.
Russian Journal of Bioorganic Chemistry 1991, 17 (12):1665-1688