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Syntheses and Reactions of 1′,2′-Unsaturated 2′,3′-Seconucleoside Analogues

✍ Scribed by Valerije Vrček; Vesna Čaplar

Publisher
John Wiley and Sons
Year
1995
Tongue
German
Weight
612 KB
Volume
78
Category
Article
ISSN
0018-019X

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✦ Synopsis

The 1',2'-unsaturated 2',3'-secoadenosine and 2',3'-secouridine analogues were synthesized by the regioselective elimination of the corresponding 2',3'-ditosylates, 2 and 18, respectively, under basic conditions. The observed regioselectivity may be explained by the higher acidity and, hence, preferential elimination of the anomeric H-C(1') in comparison to H-C(4). The retained (tol-4-yl)sulfonyloxy group at C(3') of 3 allowed the preparation of the 3'-azido, 3'-chloro, and 3'-hydroxy derivatives 5-7 by nucleophilic substitution. ZnBr, in dry CH2C12 was found to be successful in the removal (85%) of the trityl group without any cleavage of the acid-sensitive, ketene-derived N,O-ketal function. In the uridine series, base-promoted regioselective elimination (+ 19), nucleophilic displacement of the tosyl group by azide (+20), and debenzylation of the protected N(3)-imide function gave 1',2'-unsaturated 5'-O-trityl-3'-azido-secouridine derivative 21. The same compound was also obtained by the elimination performed on 2,2'-anhydro-3'-azido-3'-deoxy-5'-~-~rityl-2',3'-secouridine (22) that reacted with KO(f-Bu) under opening of the oxazole ring and double-bond formation at C(1').

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Nucleoside numbering is used for 2',3'-seconucleosides, systematic names are given in the Exper. Part.

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