3 -Deoxy-3 -fluoroadenosine

The same conditions led to decomposition in an attempt to prepare 2 -deoxy-2-fluoroadenosine from 2 -deoxyadenosin-2-amine. The reaction was successful when applied to 3, 5 -di-0-acetyl-2 -deoxyadenosin-2-amine giving the 2-fluoro derivative 2. ... 

Maruyama, T., Utzumi, K., Sato, Y. and Richman, D. D. (1994) Synthesis and anti-HIV activity of 2-substituted 2 -deoxy-2 -fluoroadenosines. Nucleosides Nucleotides, 13, 1219-1230. 

Since 1976 a number of 2 -substituted 2 -deoxynucleoside 5 -diphosphates have been shown to be mechanism-based inactivators of the ribonucleotide reductases from a variety of sources (Table I). This work was extended by Stubbe and Kozarich 50, 51), who studied the reaction of several 2 -halo-substituted 2 -deoxynucleoside 5 -diphosphates with RDPR. Incubation of RDPR with CIUDP, 2 -deoxy-2 -fluoroadenosine 5 -diphosphate (FADP), or 2 -deoxy-2 -fluorocytidine 5 -diphosphate (FCDP) resulted in time-dependent enzyme inactivation, concomitant and stoichiometric loss of all substituents from the ribose moiety, increase in the UV-Vis absorbance of the protein near 320 nm, and... 

Deoxy-5-ethyluridine, E-2 2 -Deoxy-2 -fluoroadenosine, D-63 5 -Deoxy-2-fluoroadenosine, D-64... 

Chloro-2-deoxyarabinose D-form Di-Et dithioacetal, C-74 2-Chloro-2-deoxyascorbic acid L-form, C-78 2-Chloro-2-deoxyglucose D-form, C-85 2-Chloro-2-deoxylyxose a-D-Pyranose-/orw, C-95 2-Chloro-2-deoxyxylose D-Pyranose-/orm, C-108 2-Deoxy-2,2-difluoro-flrfl6mo-hexose D-form, D-55 2 -Deoxy-2 -fluoroadenosine, D-63 1 -(2-Deoxy-2-fluoro- p-D-arabinofuranosyl)uracil, D-66 2-Deoxy-2-fluoroarabinose a-L-Furanose-/<3rm 1,3,5-Tribenzoyl, D-68 2-Deoxy-2-fluoroarabinose p-D-Furanose-/orm, D-68 2-Deoxy-2-fluoroarabinose a-D-Pyranose- brm, D-68 2-Deoxy-2-fluoroarabinose p-D-Pyranoae-/orm, D-68 2-Deoxy-2-fluoroarabinose D-form, D-68 2 -Deoxy-2 -fluoro-ara -aristeromycin, D-70 2-Deoxy-2-fluoroascorbic acid L-form, D-71 2 -Deoxy-2 -fluorocytidine, D-72... 

A rapid synthesis of 2 -deoxy-2 -fluoroadenosine Involves the use of DAST on a suitably protected ara-A derlvative.85 A number of purine nucleosides containing the 2 -deo3qr-2 -fluoro-p-D-arabinofuranosyl moiety (48) have been prepared from glycosyl bromide and purine bases the guanosine analogue (48,... 

Analogues of tiazofurin adenine dinucleotide (TAD) containing 2 -deoxy-2 -fluoroadenosine, 3 -deoxy-3 -fluoroadenosine and 2 -deoxy-2 -fluoro-ara-A, have been synthesized and evaluated as inhibitors of IMP dehydrogenase. ... 

For the synthesis of 2 -deoxy-2 -fluoroadenosine (2a) from ara-A, smaller 3, 5 - protecting groups (such as methoxymethyl, benzyl, or methojgrbenzyl groups) appear to be more favorable for ara-A to assume the presumably favored C-3 endo conformation than the trityl groups (which promote C-3 endo to C-2 endo conformational shift). In order to prepare 3, 5 -protected ara-A, 3, 5 -0-(l,l,3,3-tetraisopropyl)disiloxanyl-N -benzoyladenosine (54, Scheme 10) was triflylated, and the... 

We also synthesized 3 -fluoroadenosine. In our case, the starting material was again 2, 5 -di-0-trityl-N -trityladenosine 32 (Scheme 5), which had already served as the starting material for the synthesis of 2 -deoxy-2 -fluoroadenosine (2a, Scheme 11). 

An improved synthesis of 2 -deoxy-2 -fluoroadenosine has been described, involving a sequence of two inversions of configuratkMi at C-2 of an adenosine derivative, whilst the 2 -deoxy-2 -fluoroderivatives of a wide range of purine nucleosides have been made by glycosyl transfn 6tMn 2 -deoxy-2 -fluorouridine uring diymidine phosphorylase and purine nucleoside phosphc lase. ... 

Deoxy-5 -fluoroadenosine (911) and the analogs 910, 912, 913 were prepared by coupling of 5-deoxy-5-fluoro-D-ribofuranose and 6-chloro-purine. 2, 5 -Dideoxy-5 -fluoroadenosine (914) was prepared through a displacement reaction of the corresponding 5 -0-tosyl precursor with fluoride (BU4NF in DMF). The carbocyclic nucleosides 915 and 916 have been prepared and their antiviral activities evaluated. 

Figure 13.18 Biosynthesis of fluorinated metabolites via 5 -deoxy-5 -fluoroadenosine...

Synthesis of 2 -Deoxy-2 -a-fluoroadenosine Using a Protection Strategy with 3and 5 -Hydroxyl Groups... 

FddA from 2 -Deoxy-2 -a-fluoroadenosine Until recently, the introduction of a fluoro group to the P-side of C-2 has been quite difficult, as described earlier. Accordingly, a novel strategy that involves the inversion of C-2 of 2 -deoxy-2 -a-fluororiboside to its 2 -p-fluoro epimer was developed by Marquez and co-workers (see Scheme 7.12). In their synthesis, A -benzoyl-2 -deoxy-2 -a-fluoroadenosine (43a) was converted to 3 -0-... 

A convenient synthesis of 5 -deoxy-2-fluoroadenosine from guanosine has been reported. Ring-opening of l-(2,3-anhydro-P-D-lyxofuranosyl)-cytosine and -uracil with ammonium bromide, iodide, azide, and thiocyanate in refluxing ethanol has been used to prepare l-(3-deoxy-3-halogeno-P-D-arabinofuranosyl)-... 

Some 4, S -unsaturated-S -fluoroadenosine nucleosides are described in Chapter 20 as well as some purine nucleosides containing the 2 -deoxy-2 fluoro- -D-arabinofuransoyl moiety. A number of dideoxymonofluoro- and dideo difluoro-a-D-glucopyranosyl phosphates have been prepared in order to study their relative rates of acid hydrolysis. The synthesis of a fluorinated 3-deoj -D-glyceric add phosphonate is discussed in Chapter 17 and the conversion of a l,3-anhydro-2-deojty- 2,2-difluoro-D-hexose derivative into a hydrolytically stable thromboxane A2 mimic is covered in Chapter 24. 

Ohrui H, Kohgo S, Hayawaka H, Kodama E, Matsuoka M, Nakata T, Mitsuya H (2007) 2 -deoxy-4 -C-ethynyl-2-fluoroadenosine a nucleoside reverse transcriptase inhibitor with highly potent activity against wide spectrum of HIV-1 strains, favorable toxic profiles, and stability in plasma. Nucleosides Nucleotides Nucleic Adds 26 1543-1546... 

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