Difluoro -2 -deoxyuridine

The third synthetic application is demonstrated by alkenylation of 5-iodouracil and 5-iodouridine [Eq.(15)]. These iodides were allowed to couple with alkenyl(difluoro)methylsilanes to afford 5-alkenyl-substituted uracils and uridines, respectively, which are potent antitumor or antiviral agents. It is noteworthy that unprotected 5-iodo-2-deoxyuridine could be converted into the corresponding cross-... 

Fig. 8 CuAAC reaction for in vivo labeling of DNA and RNA. a Schematic representation for in vivo fluorescent labeling of DNA and RNA molecules using metaboUcally incorporated EdU (or EU) and CuAAC reaction, b Detection of vims infection using the ceU-selective incorporation of dF-EdU and CuAAC reaction [102-104]. CuAAC copper(I)-catalyzed azide-aUcyne cycloaddition, EdU 5-ethynyl-2-deoxyuridine, EU 5-ethynyluridine, dF-EdU 2 -deoxy-2, 2 -difluoro-5-ethynyluridine...

Various 2 -C -alkylated derivatives of carbocyclic 5-methyluridine have been prepared, as have 6 -alkoxy and -acyloxy-derivatives of carbocyclic thymidine (119), in order to test the effect of the structural alterations on DNA/RNA duplex stability. A short and high-yielding synthesis of carbocyclic bromo-vinyl-deoxyuridine (BVDU) has been described, involving a cyclopentylamine derivative as an intermediate. Carbocyclic BVDU and carbocyclic 2 -deoxy-guanosine have been made by a modification of an earlier route to carbocyclic 2 -deoxynucleosides, involving a microbiological reduction. Racemic difluoro-carbocyclic nucleosides of type 120 have been made via the fluorination of ( )-JV-Boc-2-azabicyclo[2.2.1]hept-5-en-3-one (see Vol.28, p.284), and the (+)-enan-tiomer of 2-azabicyclo[2.2.1]hept-5-en-3-one has been converted into the (—)-enomtiomer, which is of considerable use in the synthesis of carbocyclic nucleosides in the o-series. ... 

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