Nucleic acid complex
A complex, nucleic acid technology, applied in the field of nucleic acid complexes, can solve problems such as limited scope of application
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Embodiment 1
[0721] Synthesis of Embodiment 1 Linker Unit 1
[0722] Synthesis of compound 9
[0723] [chemical formula 115]
[0724]
[0725] Process 1
[0726] Dimethyl 5-hydroxyisophthalate (compound 1, manufactured by Wako Pure Chemical Industries, Ltd., 5.0443 g, 24 mmol) was dissolved in tetrahydrofuran (manufactured by Wako Pure Chemical Industries, Ltd., 25 mL), and 2-(tert-butoxycarbonyl Amino)-1-ethanol ((Tokyo Chemical Industry Co., Ltd., 4.0343g, 25.03mmol), and triphenylphosphine supported on the polymer (Aldrich Co., 6.61g, 25.2mmol), and then under ice cooling, add 40% diisopropyl azodicarboxylate (DIAD) toluene solution (manufactured by Tokyo Chemical Industry Co., Ltd., 13.26 mL, 25.2 mmol), stirred overnight at room temperature. The reaction solution was filtered, and the filtrate was distilled off under reduced pressure, and then The residue was purified by amino silica gel column chromatography (hexane / ethyl acetate=95 / 5 to 80 / 20) to obtain compound 2 (5.3071 g, y...
Embodiment 2
[0751] Synthesis 2 of embodiment 2 linker unit
[0752] Synthesis of Compound 19
[0753] [chemical formula 116]
[0754]
[0755] Process 9
[0756] Using Compound 2 (2.1 g, 5.940 mmol) synthesized in Step 1 of Example 1, Compound 10 was quantitatively obtained by the same method as in Step 4 of Example 1.
[0757] ESI-MS m / z: 254 (M+H) +
[0758] 1 H-NMR (DMSO-D6) δ: 3.26 (2H, t, J = 5.1 Hz), 3.90 (6H, s), 4.30 (2H, t, J = 5.1 Hz), 7.77 (2H, dd, J = 1.5 , 0.8Hz), 8.13 (1H, dd, J=1.4, 0.7Hz).
[0759] Process 10
[0760] Compound 10 (0.427 g, 1.686 mmol) synthesized in Step 9 and 6-azidohexanoic acid synthesized by the method described in Organic & Biomolecular Chemistry, Vol. 13, pp. 1778-1791, 2015 were used Pyrrolidinyl ester (0.6 g, 2.360 mmol), compound 11 (0.248 g, yield 38%) was obtained by the same method as in step 5 of Example 1.
[0761] ESI-MS m / z: 393 (M+H) +
[0762] 1 H-NMR (CDCl 3)δ: 1.37-1.44 (2H, m), 1.64-1.69 (4H, m), 2.23 (2H, t, J = 7.5Hz)...
Embodiment 3
[0795] Synthesis of embodiment 3 linker unit 3
[0796] Synthesis of compound 22
[0797] [chemical formula 117]
[0798]
[0799] Process 18
[0800] (a); Compound 13 (10 mg, 17.9 μmol) synthesized in the procedure 12 of Example 2 was dissolved in a mixed solution of tetrahydrofuran (90 μL) and phosphate buffer (90 μL), and carboxyl-(12 low ethylene glycol) was added Ethylamine (manufactured by Thermo Scientific, 22.1 mg, 35.8 μmol) was stirred at room temperature under an argon atmosphere for 1 h. The solvent was distilled off under reduced pressure, extracted with chloroform and 10% aqueous citric acid solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude product of Compound 17.
[0801] ESI-MS m / z: 1564 (M+H) +
[0802] (b); Compound 13 (10 mg, 17.9 μmol) synthesized in the procedure 12 of Example 2 was dissolved in a mixed solution of tetrahydrofuran (90 μL) and phosphate buffer (90 μL), and c...
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