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2005
Nucleic acids
U 0700
Synthesis of C-Nucleoside Analogues Starting from 1-(Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)-4-phenyl-but-3-yn-2-one.
33- 252 —
To enlarge the class of spacer iso-C-nucleosides, the ynone system (V) is used as a
precursor for the construction of different types of heterocycles. Thus, treatment of (V)
with amidinium salts (VI), hydrazine, sodium azide, and aminobenzimidazole (X)
yields the corresponding heterocycles including iso-C-nucleoside (XI) with a more
complex heterocyclic unit whose exact structure determination is impossible by NMR
measurements. The branched-chain altropyranoside (I) can be synthesized in six steps
from D-glucose. — (TABOADA, L. H.; FEIST, H.; SUAREZ, J. Q.; MICHALIK, M.;
PESEKE*, K.; J. Carbohydr. Chem. 23 (2004) 5, 325-335; Fachber. Chem., Univ.
Rostock, D-18051 Rostock, Germany; Eng.) — H. Hoennerscheid
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