Glycoside compound, amide compound, and method for producing polynucleotide using these compounds
A technology of amide compounds and manufacturing methods, which is applied in the preparation of organic compounds, preparation of sugar derivatives, chemical instruments and methods, etc., can solve the problems of unsatisfactory yield and purity, and achieve the goal of improving yield and purity Effect
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[0266] Hereinafter, in order to demonstrate this invention in detail, an Example is given. However, the present invention is not limited at all by these Examples and the like.
[0267] In this specification, the following abbreviations are used.
[0268] TPM=(1-(4-methylbenzenesulfonyl)propan-2-yl)oxy)methoxy)methyl; A=adenine, G=guanine, C=cytosine, U=uracil.
[0269] Manufacture of TPM amidate U
manufacture example 1
[0271] 1) Manufacture of TPMizing agent (TPMR)
[0272] [Chemical formula 41]
[0273]
[0274] Bis(methylthiomethyl)ether (5.9 g, 0.043 mol) was dissolved in dry tetrahydrofuran (THF) (60 mL), molecular sieve 4A (5.9 g) was added, and the mixture was stirred for 10 minutes. After cooling the mixture to -50°C, N-iodosuccinimide (NIS) (11.5 g, 1.19 eq.) and trifluoromethanesulfonic acid (TfOH) (0.11 mL, 0.030 eq.) were added sequentially. To the mixture was added dropwise a solution of 1-(4-methylbenzenesulfonyl)propan-2-ol (10 g, 1.09 eq.) (manufactured by ENAMINE Ltd.) in acetonitrile (20 mL), and the mixture was heated to -50~ Stir at -45°C for 4 hours. After adding triethylamine (4.0 mL) dropwise to the reaction solution, the temperature was raised to -30 to -20°C, and then to sodium thiosulfate pentahydrate (17.1 g) previously cooled to 5 to 10°C in an ice-water bath. , sodium bicarbonate (6.0 g) and water (130 mL) were added to the above reaction solution. Ethyl ac...
manufacture example 2
[0279] 2) Manufacture of TPM-U-2
[0280] [Chemical formula 42]
[0281]
[0282] To U-1 (3.3 g, 6.78 mmol) was added anhydrous toluene (16.5 mL, 5 vol / wt), the mixture was concentrated under reduced pressure to 3 vol / wt, and anhydrous toluene (6.6 mL, 2.0 vol / wt) was further added , the mixture was concentrated under reduced pressure to 3 vol / wt. Anhydrous tetrahydrofuran (6.6 mL, 2.0 vol / wt) was added, the mixture was cooled to about -55°C, PMMR (3.09 g, 10.17 mmol, 1.5 eq.) was added dropwise, and the mixture was washed thoroughly with THF 2 mL. NIS (2.06 g, 9.15 mmol, 1.35 eq.) was added to the mixture, and TfOH (0.72 mL, 8.14 mmol, 1.2 eq.) was added dropwise at -55 to -45°C. After the mixture was stirred at -55 to -45°C for 1 hour, a mixture consisting of sodium thiosulfate pentahydrate (3.3 g), sodium bicarbonate (1.12 g), water (22 mL) and toluene cooled with an ice-water bath was added. The reaction solution was added to the solution. The mixture was stirred in...
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