Uridine, 2 -deoxy , 5-iodo

Shaw synthesis, 3, 109 Uridine, 2 -deoxy-5-iodo-as pharmaeeutical, 1, 160 Uridine 5 -monophosphate biosynthesis, 1, 88 Uridylic acids occurrence, 3, 142 Urispas... 

The reaction has been extended (106) to the nucleoside field and provides a means for the direct iodination of suitably protected nucleosides. Thus treatment of 2,3-O-isopropylidene uridine (68) with tri-phenylphosphite methiodide in N,2V-dimethylformamide at room temperature afforded the corresponding crystalline 5-deoxy-5-iodo analog 69 in 77% yield. 

Selective replacement of primary hydroxyl groups in carbohydrates by iodine atoms has been achieved by using the Rydon reagent, namely, methyltriphenoxyphosphonium iodide.368 Treatment of methyl 3,4-O-isopropylidene-jS-D-galactopyranoside with the phosphonium salt in benzene for 48 hours at room temperature yielded 60% of the 6-deoxy-6-iodo derivative,369 and reaction of thymidine, uridine, and 2,2 -anhydrouridine in N,N-dimethylformamide afforded 5 -deoxy-5 -iodo derivatives in yields of 63, 65, and 31%, respectively.370... 

Of incidental interest is the observation that an w-chlorine atom may be replaced by iodine under Oldham and Rutherford s conditions, without affecting secondary sulfonyloxy groups. Thus, Levene and Tipson107 found that 5-chloro-5-deoxy-2,3-di-0-tosyl-uridine affords the corresponding 5-deoxy-5-iodo derivative plus sodium chloride on the other hand, methyl 4-chloro-4-deoxy-2,3,6-tri-0-tosyl-a-D- glucoside gives117 the 4-chloro-4,6-dideoxy-6-iodo derivative. These observations, taken... 

Arylhalide 5 -iodo-2 -deoxy- uridine monophosphate Thymidine kinase Both iodine and nucleotide covalently incorporated. Only nucleotide incorporation parallels inhibition of enzyme activity (Chen et al., 1976). 

Deoxy-2 -iodo-3 -0-TEDMS uridine derivative 146, readily available from uridine via 2,2 -anhydrouridine, was subjected to the above-mentioned procedure. After removal of the monomethoxytrityl (MMTr) group and subsequent acetylation with AC2O in pyridine. 

The RNA dinucleotide phosphorothiolate, 3 -(thioinosylyl)-(3 -5 )-uridine 59 (IspU) containing a 3 -S-phosphorothiolate linkage has been prepared from 9-(3-deoxy-3-iodo-P-D-xylofuranosyl)hypoxanthine using Arbuzov chemistry. IspU was found to be a substrate for several RNA hydrolysing enzymes and is also labile to acid, base and silver ions. The analogue has also been used to study the... 

When 6 -deoxy-5 -iodo-2, 3 -0-isopropylideneuridine (203) is treated with silver dibenzyl phosphate or with silver tribenzyl pyrophosphate, the protected 5 -nucleotide (205, R = benzyl or dibenzyl phosphoric) was obtained after removal of the protecting groups, this gave uridine 5 -phos-phate (206, R = H) and uridine 5 -pyrophosphate (R = POsHa). It is possible that, in the formation of (205) from (203), anhydronucleoside (204) was an intermediate which underwent attack by the phosphoric... 

Uridine has been converted in seven steps into 5 -amino-3, 5 -dideoxyuridine (66), related to the 4, 5 -unsaturated structure found in the mureidomycin antibiotics. Some 5 -Amino-5 -deoxy-5-iodo-pyrrolopyrimidine nucleosides such as 67 (X = Cl, NH2) have been prepared by sodium salt glycosylation procedures, and shown to be powerful adenosine kinase inhibitors. ... 

Iodo-2 -deoxy- uridine Thymidine kinase Enhanced activity loss on photolysis thymidine protects 124... 

Cyclouridine, 39B, 322 5-Bromo-2 -deoxyuridine, 31B, 183 1 i3-D-Arabinofuranosyl-5-bromouracil, 39B, 324 5-Bromouridine, 31B, 183 2 -Chloro-2 -deoxyuridine, 38B, 455 5-Chloro-2 -deoxyuridine, 39B, 324 5-Chlorouridine, 37B, 248 -Fluoro-2 -deoxy-/3-uridine, 29, 710 -Iodo-2 -deoxyuridine, 30B, 204 -lodouridine, 35B, 276... 

Verheyden and Moffatt have prepared l-(5-deoxypent-4-enofuranosyl) derivatives of uridine, thymidine, cytidine, and 2 -deoxycytidine by dehydrohalogen-ation of the acetylated 5 -deoxy-5 -iodo-nucleoside with either silver fluoride in pyridine or DBN (Scheme 89). ° Similar treatment of 3, 5 -dideoxy-3, 5 -di-iodothymidine (235) furnished the dihydrofuran derivative (236). Addition reactions of 4, 5 -unsaturated derivatives of nucleosides are mentioned in Chapter 21. 

A satd. soln. of iodine in methylene chloride added dropwise during 10 min. to a stirred soln. of l-(5-deoxy-2,3-0-isopropylidene- -D-ery//iro-pent-4-enofuranosyl)-uracil in the same solvent in the presence of finely divided AgF until a permanent iodine color persists -> 5 -deoxy-4 -fluoro-5 -iodo-2, 3 -0-isopropylidene-uridine. Y 99%. G. R. Owen, J. P. H. Verheyden, and J. G. Moffat, J. Org. Chem. 41, 3010 (1976). 

A new synthesis of 3 -deoxy-3 -nitrothymidine involves displacement of an up -iodo-substituent by nitrite ion in DMSO in the presence of phloroglucinol. The (hydroxylamino)nucleoside 65 has been made by reduction of a C-3 nitrone with NaBHsCN, and related 0-alkylhydroxylamines were also described, prepared by reduction of O-alkyloximes. Similar O-alkyloximes at both C-2 and C-3 of uridine have been prepared as potential inhibitors of ribonucleoside diphosphate reductase. ... 

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