Abstract
The β-ribofuranosylazide1 is transformed after usual derivatization by suitable protecting groups into the P–N-ylid2, which gives the corresponding N-Glykosyl-N-alkylcarbodiimides4 and a small amount of the glykosylisocyanatde-rivative3 by reaction with alkylisocyanates. The carbodiimides4 were reacted with hydrazoic acid to give the alkylaminotetrazolnucleosides5 and finally the free nucleosidanalogs6. In the case of5 c the 5-aziridinyltetrazolnucleosid5 h was formed by an usual neighbouring group reaction. In addition the compound1 is transformed into the 3′,5′-diprotected anchor derivative7 by reaction withTIPSCl2. The latter could be transformed by usual steps into the alkylaminotetra-zolnucleosides8 with a free 2′-OH group. In the next step the 2′-p-tolylthiocarbo-nates9 were prepared followed by transformation to the 2′-desoxynucleosides10 by means of tributyltinhydride. Finally the free 2′-desoxynucleosides11 were prepared. By reacting the carbodiimides4 with phenylisocyanate a mixture of the two possible regiouretidinonnucleosidderivatives12 and13 are formed. In the case of the N-glykosyl-N-allylcarbodiimide4 d only the one isomer13 d arises.
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Herrn Prof. Dr.A. Neckel mit den besten Wünschen zum 60. Geburtstag gewidmet.
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Knotz, H., Zbiral, E. Glykosylazide als Ausgangsbasis zur Gewinnung von Nucleosidanalogen, 3. Mitt. Synthese von Alkylaminotetrazol- und Uretidinonnucleosiden. Monatsh Chem 117, 1437–1460 (1986). https://doi.org/10.1007/BF00810753
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DOI: https://doi.org/10.1007/BF00810753