Thymidine -5 -0-trityl

C24H25NO 127927-43-9) see Saquinavir tris(trimethylsilyloxy)ethylene (CiiH2g03Si3 69097-20-7) see Saquinavir (-)-(S)-l-trityl-2-(aminomethyl)pyrrolidine (C24H26N2 98598-84-6) see Remoxipride 5 -0-trityl-2,3 -anhydro thymidine (C29H24N2O4 25442-42-6) see Zidovudine trityl chloride... 

P-NMR spectroscopic studies on the reaction course of the dinucleotide synthesis from 3 -0-acetylthymidine 5 -phosphate (pT-Ac) (180a) and 5 -0-trityl-thymidine (Tr-T) in the presence of triisopropylbenzenesulfonyl chloride (TPS) confirm the metaphosphate hypothesis 123,124). Successive addition of 0.5 equiv. 

Treatment of O-benzoyl anhydrothymidine 64 (R1 =Me R2 = COPh) with MgX2 (X = Br, I) in toluene at 100 °C afforded halo-substituted thymidines 65 (Nu = Br, I) in 70-75% yields <1995NN307, 1995TL873>. Alkylation of O-trityl anhydrothymidine with methyl triflate followed by reaction with NaBr or Nal gave the corresponding N(3)-methylated thymidines 65 (Nu = Br, I) in 70-90% yields <1993TL8411>. 

Their tritylation and tosylation studies130 also indicated that the ring structure in thymidine is of the furanoid form. These aspects have been... 

Threose, 4-acetamido-4-deoxy-D-, 179 Thymine, l-(5-0-acetyl-2-0-p-tolylsulfo-nyl-/S-D-ribofuranosyl)-, 245 —, l-[2-0-(methyIsulfonyl)-5-0-trityl-/3-D-ribofuranosyl]-, 245 —, l-(5-thio-D-xylopyranosyl)-, 211 —, l-(2-0-p-tolylsulfonyl-5-0-trityl-/3-D-ribofuranosyl)-, 245 Thymidine, 4 -thio-a-D-, 223 —, 4 -thio-/3-D-, 223... 

Hakimelahi has reported a novel strategy for the synthesis of N -purine acyclic nucleosides, in which the key step involves the reaction of [2-(p-methoxyphenyloxy)ethoxyl]methyl chloride and iV -tritylated nucleobases, followed by concomitant self-detritylation. 7-[(2-Hydroxyethoxy)methyl] guanine was phosphorylated by both HSV- and Vero-cell thymidine kinases to yield (92), and was found to have more potent cellular toxicity than acyclovir, while the adenine parent was phosphorylated by neither kinase. In addition, the N -adenine acyclic nucleoside phosphonate (93) was synthesised by alkylation of adenine with 3-bromopropionitrile to yield AT -(cyanoethyl)adenine, which upon... 

To date, the sugar ring structure of only one desoxyribosyl nucleoside (namely, thymidine) is known. In 1935, Levene and Tipson - found that thymidine condenses with trityl chloride in the presence of dry pyridine to give a crystalline monotrityl-thymidine. From their previous proof of the structure of monotrityl-uridine as the 5-trityl ether, it seemed probable that the thymidine ether is 5-trityl-thymidine. This was confirmed by tosylation, to give tosyl-trityl-thymidine, followed by treatment with sodium iodide in acetone under standard conditions. 

There was practically no reaction with sodium iodide, indicating that the tosyl group was not situated at position (5) and that the tosylation product was 3-tosyl-6-trityl-thymidine. Hence, the ether is 5-trityl-thymidine, and thymidine can be assigned a furanose ring. This conclusion received confirmation from their observation that, unlike guanosine and inosine, thymidine does not react with boric acid and therefore does not possess two adjacent cia hydroxyl groups. 

Anhydronucleosides are usually prepared from appropriate mono- or di-sulfonates [1]. l-(2-Deoxy-3,5-anhydro)- -D-r/ireo-pentosylthymine (96), an example of the oxetane-type of anhydronucleoside, was prepared from dimesyl thymidine by the action of an alkali. The first synthesis of 2, 3 -dideoxy-2, 3 -didehydro-thymidine (d4T) was accomplished in 1966 by Hor-witz et al. from this compound, which can be now prepared in quite large scale according to a slightly modified procedure proposed by the group from Bristol-Myers. The 5 -tritylated derivative of 3 -0-mesyl-thymidine was converted into 3, 2-anhydroucleoside 95, from which... 

Use Biochemical research. Also available as trityl thymidine and as tritiated thymidine in a radioactive form. 

Scheme 6 illustrates the use of these protecting groups in the phosphorylation of 2 -deoxynucleosides by Michelson and Todd. 5 -0-Trityl-thymidine (110) was phosphorylated with dibenzyl phosphorochloridate (44) to (111), which, after treatment with 80% acetic acid, afforded thymidine 3-(benzyl phosphate) (112). Catalytic hydrogenolysis of (112) gave thymidine 3 -phosphate. Acetylation of (110) yielded the 3 -acetate (114) which, on detritylation to (115), followed by phosphorylation, catalytic reduction, and deacetylation, gave thymidine 5 -phosphate (116), identical with the thymidylic acid obtained by enzymic hydrolysis of 2 -deoxyribonueleic acid. A rather similar sequence was applied to the preparation of the 2 -deoxycytidine analogs of (113) and (116). 

Aq. Na-thiosulfate added to a soln. of bis-2,4-dinitrobenzenesulfenyl-5 -0-trityl-thymidine in methanol, after 4 hrs. coned, in vacuo 5 -0-tritylthymidine. Y ... 

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