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2005
Nucleic acids
U 0700
Synthesis of Substituted 1-\C\-Phenyl-D-tetritols and 1-C-(1H-Pyraby Ring Transformation of 2-Formylglycals. — The push-pull
33- 251 zol-4-yl)-D-tetritols
activated double bond in formylglycal (I) enables the nucleophilic attack of dinucleophiles (II) at C-1 under ring opening and subsequent cyclization involving the formyl
group. This ring transformation yields the expected isophthalic acid derivatives (III).
However, the reaction of (IIIb) with ethyl chloroacetate (IV) provides not the desired
benzofuran derivative but the corresponding ethoxycarbonylmethoxy-isophthalic acid
diethyl ester (V). The push-pull functionality of (I) also allows reactions with
1,2-N,N'-dinucleophiles like (VI) to furnish the corresponding C-nucleoside analogues,
e.g. (VII). — (MONTERO, A.; MICHALIK, M.; FEIST, H.; REINKE, H.; RUDLOFF,
I.; PESEKE*, K.; J. Carbohydr. Chem. 23 (2004) 5, 313-324; Fachber. Chem., Univ.
Rostock, D-18051 Rostock, Germany; Eng.) — H. Hoennerscheid
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