Thymidine chloride

CH3SCH20)(CH2)3C02H, 2,6-dichlorobenzoyl chloride, Pyr, CH3CN, 70% yield. The MTMB group was selectively introduced onto the 5 -OH of thymidine. 

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... 

Figure 12 Gradient separation of bases, nucleosides and nucleoside mono- and polyphosphates. Column 0.6 x 45 cm. Aminex A-14 (20 3 p) in the chloride form. Eluent 0.1 M 2-methyl-2-amino-l-propanol delivered in a gradient from pH 9.9-100 mM NaCl to pH 10.0-400 mM NaCl. Flow rate 100 ml/hr. Temperature 55°C. Detection UV at 254 nm. Abbreviations (Cyt) cytosine, (Cyd) cytidine, (Ado) adenosine, (Urd) uridine, (Thyd) thymidine, (Ura) uracil, (CMP) cytidine monophosphate, (Gua) guanine, (Guo) guanosine, (Xan) xanthine, (Hyp) hypoxanthine, (Ino) inosine, (Ade) adenosine, (UMP) uridine monophosphate, (CDP) cytidine diphosphate, (AMP) adenosine monophosphate, (GMP) guanosine monophosphate, (IMP) inosine monophosphate, (CTP) cytidine triphosphate, (ADP) adenosine diphosphate, (UDP) uridine monophosphate, (GDP) guanosine diphosphate, (UTP) uridine triphosphate, (ATP) adenosine triphosphate, (GTP), guanosine triphosphate. (Reproduced with permission of Elsevier Science from Floridi, A., Palmerini, C. A., and Fini, C., /. Chromatogr., 138, 203, 1977.)...

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. 

Amino-l,2,4-benzotriazine 1,2-dioxide Thin layer chromatography Thymidine-5 -phosphate iV,iV,iV, iV -Telramclhylphcnylcncdiamine Tetranitromethane 3,5,4 -Trihydroxy-frans-stilbene 2-Amino-2-hydroxy-l, 3-propanediol Time-resolved light-scattering p-[meso-5-5,10,15,20-Tetra(pyridyl)porphyrin]tetra kis[ (ns-(bipyridine) chloride ruthenium(II)]... 

Thymidine dimers in which the natural phosphodiester linkage has been replaced by a 2,5-disubstituted tetrazole ring have been synthesized and have been incorporated into oligodeoxynucleotides <02HCA2847>. The synthesis of mono- and bis-3-substituted thymidine derivatives with a polycyclic tetrazole linker (l,5-bis(tetrazol-5-yl)-3-oxapentane) has been reported <02TL1901>. a-Methylene tetrazole-based peptidomimetics were synthesized for inhibition studies of HIV protease <02JCS(P1)172>. A catalytic amount of tetrazole was found to be useful in the syntheses of symmetrical P,P -dialkyl partial esters of methylenebisphosphonic acid from the corresponding acid chloride via a facile two-step, one-... 

Add the tosyl chloride solution dropwise to the stirred, cooled solution of thymidine, and when this is complete, stir at 0°C. 

Thymidine (127) Acetal CH3CN THAC1 Amb. Tosyl chloride 2 70 3 0 — 71... 

Thus, 3, 5 -di-0-(f-butyldimethylsilyl)thymidine (211) is sulfonylated by 2,4,6-triisopropylbenzenesulfonyl chloride (TIPS-CI) to furnish the 4-O-TlPS derivative 212 in 93% yield. Amination with 2-(methylam-ino)ethanol gives rise to 72% of 213 (87TL282I). 

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... 

A potentially attractive route to 0-roethylnucleosldes is based on the use of the [[2-(methylthio)phenyl]thio]methyl group for the protection of primary and secondary hydroxy functions.This protecting group is stable under both acidic and basic conditions and functions as a latent 0-methyl group. For example, 5 -0-[[[2-(methylthio)phenyl]thio]methyl]-2 -deoxythymldine (105) is readily converted into 5 -0-methylthymidine in 68Z yield by treatment with tributyltin hydride and azobls(isobutyronitrile). Alternatively, deprotection to give thymidine can be accomplished using mercury (II) chloride in aqueous acetonitrile. 

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. 

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