Thio thymine

Mol) l-(3,5-Di-0-benzoyl-2-desoxy-/3-D-ribosyl)-4-thio-thymin werden unter Riihren mit 16 g aktivem Raney-Nickel in 500 ml Athanol 15 Min. unter RiickfluB gekocht. Man filtriert und dampft i. Vak. zur Trockne ein. Der Ruckstand wird in Athanol gelost, mit Aktivkohle behandelt und abgekiihlt. Das Hydrierungsprodukt fallt in groBen farblosen Kristallen aus Ausbeute 2,8g (64% d.Th.) F 135-136°. 

Initially, most or even all known MALDI matrices were acidic compounds, such as benzoic and cinnamic acid derivatives. However, the acidic medium is not well-suited to keeping noncovalently bound complexes intact. In the 1990s, a couple of groups therefore introduced a number of nonacidic MALDI matrices such as 2-amino-4-methyl-5-nitropyridine, />ara-nitroaniline, or 6-aza-2-thio-thymine. These were shown to be beneficial for MALDI MS of noncovalent complexes—for example, to keep peptide-oligonucleotide complexes or DNA duplexes intact.However, their performance at high molecular... 

Clercq, and T. Miyasaka, Structure-activity relationships of l-[(2-hydroxyethoxy)methyl]-6-(phenyl-thio)thymine analogues effect of substitutions at the C-6 phenyl ring and at the C-5 position on anti-HIV-1 activity,/. Med. Chem. 35 337 (1992). 

Treatment of the allylic sulfoxide 1227 a with diisopropylethylamine (DIPEA) or of 1227 b with N-trimethylsilyldiethylamine 146 and TMSOTf 20 leads in ca. 90% yield to the quaternary amino derivatives 1228 and 1229 and HMDSO 7 [36] (Scheme 8.15). Tetramethylene sulfoxide 1230 reacts with silylated thymine 1231 in the presence of three equivalents of TMSOTf 20 to give the 4 -thio-nucleoside analogue 1232 and HMDSO 7 [37]. Other silylated pyrimidine, pyridine, and purine bases react analogously with cyclic sulfoxides to give 4 -thio-nucleoside analogues [37, 37a, 38]. 

Threitol, from polysaccharides, 87 Threonine, 258 Thymidine, 228, 231 6-phosphates, 220 pyrophosphate esters of, 221 5-triphosphoric acid, 228 —, 5-(rhamnosyl dihydrogen pyrophosphate), 219 Thymine, 2-thio-, 229 Thymol, 236... 

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... 

Clivio described the synthesis of an oligonucleotide building block containing a syn-cis thymine cyclobutane dimer photoproduct (216) and that of the phosphoramidite (217), and the thio analogue at the 5,6-dihydropyrimidine C5 position of the thymidyl(3 -5 )thymidine (6-4) photoproduct (218). ... 

Deoxy-2 -fluoro-4 -thio-L-ara/)z o-nucleosidcs 195 were synthesized starting from D-xylose via the 4-tluo-i,-arabinitol derivative 151 as a key intermediate (Scheme 54). Introduction of fluorine at C-2 of 151 with DAST yielded 193, which was transformed into tliio sugar 194 by oxidation and Pummerer rearrangement. Coupling of 194 witli the base and debenzylation afforded 195. The thymine analogue exhibited a moderate activity against both HSV-1 and HSV-2. 

A slow stream of ozonized oxygen passed 75 min. at -40° into a soln. of 1-acetyI-thymine in methanol, the resulting ozonide reduced with dimethyl sulfide in methanol during 12 hrs. at 0°, the crude mixture heated 20 min. at 80° with thiosemicarbazide, then treated 20 min. at 100° with 1 M NaOH 2-thio-6- azathymine. Overall Y 37%. F. e. s. M. Bobek, J. Farkas, and F. Sorm, Tetrah. Let. 1968, 1543. 

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