Thymine pentofuranosyl

Deoxy-4a-carba-p-D-eryfhro-pentofuranosyl)thymine or 4 a-carbathymidine... 

Reduction44 of 3 -keto-5 -0-tritylthymidine 33b with sodium borohydride in ethanol was also found to be stereospecific, as 80% of l-(2-deoxy-5-0-trityl-/ -D-threo-pentofuranosyl)thymine (83) was obtained. 

Gasparutto D, Ravanat J-L, GerotO, Cadet J (1999) Characterization and chemical stability of photo-oxidized oligonucleotides that contain 2,2-diamino-4-[(2-deoxy-(1-D-eryfhro-pentofuranosyl)-amino]-5(2FI)-oxazolone. J Am Chem Soc 120 10283-10286 Geimer J, Beckert D (1998) Study of radical pairs generated by photoreduction of anthraquinone-2,6-disulfonic add with thymine by Fourier transform electron paramagnetic resonance. Chem Phys Lett 288 449-458... 

Di-0-(methanesulfonyl)thymidine (248 g, 0.62 M) was added in portions to a stirred solution of sodium hydroxide (74.7 g, 1.87 M) in water (1.6 L). On addition the reaction mixture became a yellow-orange solution. This stirred solution was then heated to reflux for 2 h. Once the reaction mixture had cooled to room temperature, 6 N hydrochloric acid (100 ml) was added. The reaction mixture was concentrated in vacuo by removing 1.3 L of water. The resulting slurry was cooled in an ice bath for 2 h. The solid was then filtered and washed sparingly with ice water, and then vacuum dried to constant weight (103.7 g, 74%). The l-(3,5-anhydro-2-deoxy-p-D-threo-pentofuranosyl)thymine, melting point 188°-190°C (lit. 190°-193°C) was used without further purification. 

Endova, M., Masojidkova. M.. Budesinsky. M.. and Rosenberg, L, 3. 5 -O-Phosphonoalkylidene derivatives of l-(2-deoxy-P-D-//zrec>-pentofuranosyl)thymine. Synthesis and reactivity. Tetrahedron. 54, 11187, 1998. 

Boal, J.H., Wilk, A., Scremin, C.L., Gray, G.N., Phillips, L.R., and Beaucage, S.L., Synthesis of (2-deoxy-a- and -P-D-etyt/zr< -pentofuranosyl)(thymin-l-yl)alkanes and their incorporation into oligode-oxyribonucleotides. Effect of nucleobase-sugar linker flexibility on the formation of DNA-DNA and DNA-RNA hybrids, J. Org. Chem., 61, 8617, 1996. 

The 3 -azido-2, 3 -dideoxy-P-D- ryt/iro-pentofuranosyl nucleosides 7 shown in Fig. 2 have been prepared. Compounds 7a, 7c, 7e, 7f and 7u show significant in vitro anti-HIV activity [7, 9]. The corresponding 3 -azido-2, 3 -dideoxy-P-D-t/ir o-pentofuranosyl nucleoside epimers, in which the base is thymine [34, 35], uracil [39] and adenine [57], have also been prepared. 

A variety of l-(3-C-cyano-2,3-dideoxy-2-substituted-P-D-xy/o and -D-ribo-pentofuranosyl)thymines have been prepared by Michael addition reaction of ammonia, amines and carbon nucleophiles to unsaturated nitrile 48 (R = mono-methoxytrityl) [83]. The p-D-xy/o trans stereoisomer was usually the major or the only product. 

The 4 -acyl nucleosides 77, 78, 4 -C-branched nucleosides such as 79, and l-A -[(2 -deoxy-P-D-n7>o-pentofuranosyl)methyl] thymine, cytosine and adenosine. A number of carbocyclic nucleosides cis-l-[(2-hydroxymethyl)cyclo-pentyl]uridine, 4,4-dihydroxymethyl-(l-thymin-l-yl)cyclohexane, and the cyclopropyl-fused carbocylic analogue 81. ... 

Ag-acetate added to a soln. of 5 -deoxy-5 -iodo-3 -0-mesylthymidine in methanol, stirred and refluxed 0.5 hr. 2,5 -anhydro-l-(2-deoxy-3-0-mesyl-y -D- ry /zro-pentofuranosyl)thymine (Y 67%) allowed to react 5 days at room temp, with liq. NHg in a glass-lined steel bomb -> 2,3 -imino-l-(2-deoxy-y -D-r/zr o-pento-furanosyl)thymine (Y 84%). I. L. Doerr, R. J. Cushley, and J. J. Fox, J. Org. Chem. 33, 1592 (1968) pyrimidine nucleoside transformations via anhydronucleosides, review, s. Pure Appl. Chem. 28, 223 (1969). 

Epimer l-(2 Deoxy 4 C methyl-p-D-threo-pentofuranosyl) thymine [152141-66-7]... 

Dideoxy-2-fluoro-l,5-iminomannitol, D-566 l-(2,3-Dideoxy-2-fluoro-p-D-g-/ cero-2-pentenofuranosyl)cytosine, D-552 l-(2,3-Dideoxy-2-fluoro-p-D-g-/ cero-pent-2-enofuranosyl)thymine, D-553 l-(2,3-Dideoxy-2-fluoro-p-D-ei7 /iro-pentofuranosyl)cytosine, D-564 l-(2,3-Dideoxy-2-fluoro-p-D- /ireo -pentofuranosyl)-3,4-dihydro-4-thioxo-... 

Dideoxy-2-fluoro- p-D- threo -pentofuranosyl)-4-thiouracil, D- 567 l-(2,3-Dideoxy-2-fluoro-p-D- Areo -pentofuranosyl)thymine, D-568... 

Dibromo-2,6-dideoxy-L-mannono-1,4-lactone, D-539 2,5-Dibromo-2,5-dideoxy-D-xylono-l, 4-lactone, D-540 2",3"-Didehydro-2, 3 -dideoxy-2 -fluorocytidine, D-552 2 3 -Didehydro-2, 3 -dideoxy-2 -fluorothymidine, D-553 2, 3 -Dideh.ydro-2, 3 -dideoxy-2 -fluorouridine, D-554 2,4-Dideoxy-2,4-difluoroglucose D-form, D-561 2, 3 -Dideoxy-2 -fluorocytidine 2 -Epimer, di-Ac, D-564 2, 3 -Dideoxy-2 -fluorocytidine, D-564 l,2-Dideoxy-2-fluoro-l,5-iminomannitol D-form, D-566 l-(2,3-Dideoxy-2-fluoro-p-D-//ir o-pentofuranosyl)-4-thiouracil, D-567 l-(2,3-Dideoxy-2-fluoro-(3-D-//rr o-pentofuranosyl)thymine, D-568 2, 3 -Dideoxy-2 -fluorouridine, D-570... 

An empirical rule that predicts the sign of the Cotton effect of glycosylated uracil, cytosine, thymine, adenine, and guanine has been developed. The rule is not restricted to pentofuranosyl residues linked to N-1 of pyrimidines and to N-9 of purines, but can be applied to cyclic and acyclic sugars linked to any position on these bases. The c.d. spectra of the double-headed nucleosides 5 -deoxy-5 -(indol-l-yl)- and 5 -deoxy-5 -(6-methylthiopurin-9-yl)-adenosine and -uridine have been reported, and 3-deazapurine nucleosides have been shown to prefer a syn conformation about the iV-glycosidic bond by comparison of their c.d. spectra with those of common nucleosides. ... 

K. Agyei-Aye and D.C. Baker, Synthesis and evaluation of a series of l-(3-alkyl-2,3-dideoxy-a,P-D-e7yr/iro-pentofuranosyl)thymines, Carbohydr. Res. 183 261 (1988). 

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