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2005
Nucleic acids
U 0700
Thiosugars. Part 12. Synthesis of New 3'-O-Substituted 2',5'-Anhydro-2'-thio−α-D-pentofuranosyl Nucleoside Analogues. — Thioarabinofuranoside (I) and
20- 204 thiolyxofuranoside
(IX) are coupled with silylated uracil and thymine, (II), to yield the
uridine and thymidine analogues (III) and (X), respectively. Elaboration of these compounds affords further analogues. The nucleoside analogues are obtained as pure
α-anomers, irrespective of the anomeric configuration of the glycosyl donor. Structure,
configuration and conformation of the title analogues are elucidated by X-ray structure
analyses. Nucleoside derivatives (III), (VI), and (X) are devoid of antiviral activity.
— (VOSS*, J.; WIRSCHING, J.; SCHULZE, O.; ADIWIDJAJA, G.; GIESLER, A.;
BALZARINI, J.; DE CLERCQ, E.; Nucleosides, Nucleotides Nucleic Acids 23
(2004) 10, 1609-1623; Inst. Org. Chem., Univ. Hamburg, D-20146 Hamburg,
Germany; Eng.) — H. Hoennerscheid
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