1-(4-thio-beta-D-ribofuranosyl)uracil synthesis
- Product Name:1-(4-thio-beta-D-ribofuranosyl)uracil
- CAS Number:6741-73-7
- Molecular formula:C9H12N2O5S
- Molecular Weight:260.27
![Uridine, 3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-4'-thio-, 2'-(2,4-dimethoxybenzoate) (9CI)](/CAS/20210305/GIF/291758-14-0.gif)
291758-14-0
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Yield:6741-73-7 90%
Reaction Conditions:
Stage #1: 1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-d-ribofuranosyl] uracilwith triethylamine tris(hydrogen fluoride);triethylamine in tetrahydrofuran at 20; for 4 - 5 h;
Stage #2: with ammonia in methanol at 20;
Steps:
13
Compound 12 (1.2 G, 1.90 mmole) was dissolved in dry THF under nitrogen. TEA (1.3 mL, 9.5 mmole, 5 eq. ) and TREAT. HF (2.8 mL, 20 mmole, 10 eq. ) were added and the mixture stirred at room temperature for 4 to 5 h. The solvent was removed under reduced pressure and the residue was co- evaporated three times with toluene. Methanolic ammonia (20 mL) was added and the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (10% methanol in dichloromethane) to give Compound 13 (420 MG) in 90% yield. Compound 13 was also synthesized using literature procedure (Naka et al. in J. Am. Chem. Soc. , Vol. 122, No. 30,2000) with few modifications that resulted in significant increase in yields.
References:
WO2005/27962,2005,A1 Location in patent:Page/Page column 74
869347-03-5
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6741-73-7
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![(2R,3S,3aS,9aR)-3-hydroxy-2-(hydroxymethyl)-3,3a-dihydro-2H-thieno[2,3:4,5]oxazolo[3,2-a]pyrimidin-6(9aH)-one](/CAS/20210111/GIF/457653-25-7.gif)
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134700-25-7
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6741-73-7
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