Amino pentosaccharide related with nitrogen fixation activity of plants, and preparation method and application thereof
A technology of amino and disaccharides, applied in botany equipment and methods, preparation and application of sugar derivatives, etc., to achieve the effects of increasing the total number of roots, promoting growth, and easy operation
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Embodiment 1
[0057] Embodiment 1, the synthesis of disaccharide 3
[0058]
[0059] Compound 1 (3.2g, 5.5mmol), compound 2 (2.4g, 5.0mmol) and Molecular sieves (3g) were dissolved in 100mL of dichloromethane, cooled to -10°C in an ice bath, stirred for 0.5 hours under nitrogen protection, added 54μL (0.3mmol) of trimethylsilyl trifluoromethanesulfonate, and kept at -10°C for reaction After 0.5 hour, the ice bath was removed to allow the reactant to warm up to room temperature naturally, and 100 μL of triethylamine was added to terminate the reaction after 2 hours. The reaction solution was filtered with suction, the filtrate was concentrated under reduced pressure, and separated by column chromatography (petroleum ether: ethyl acetate = 2:1, v / v) to obtain disaccharide 3 (3.4 g, 76%) as a white foamy solid. [α] D 25 +9.6°(c 0.5 CHCl 3 ).
[0060] The structural confirmation data are as follows: 1 H NMR (300MHz, CDCl 3 ): δ8.13-7.16(m, 14H, Bz-H, Phth-H), 7.06-7.03(m, 2H, Ar-H), ...
Embodiment 2
[0061] Embodiment 2, the synthesis of disaccharide 4
[0062]
[0063] Disaccharide 3 (1.8g, 2.0mmol) was dissolved in methanol solution (40mL) containing 1% acetyl chloride, and the reaction was complete after 12 hours, neutralized with triethylamine, the reaction solution was concentrated under reduced pressure, and separated by column chromatography (Petroleum ether: ethyl acetate = 1:2) to obtain disaccharide 4 (1.4 g, 90%) as a white solid. [α] D 25 -17.0°(c 0.9CHCl 3 ).
[0064] The structural confirmation data are as follows: 1 H NMR (300MHz, CDCl 3 ): δ8.11-7.10(m, 14H, Bz-H, Phth-H), 7.06-7.03(m, 2H, Ar-H), 6.85-6.82(m, 2H, Ar-H), 5.87(dd ,1H,J 1，2 1.8Hz,J 2，3 3.5Hz, H-2), 5.46(d, 1H, J 8.2Hz, H-1′), 5.42(d, 1H, J 1.6Hz, H-1), 5.38(t, 1H, J 9.7Hz, H -4), 4.42 (dd, 1H, J 2，3 3.7Hz,J 3，4 9.7Hz, H-3), 4.11-4.01(m, 2H, 2×H-5), 3.92-3.82(m, 2H, H-3′, OH), 3.77(s, 1H, C 6 h 4 OCH 3 ), 3.61(m, 1H, H-2′), 3.46(m, 1H, H-4′), 3.38-3.30(m, 2H, 2×H-6′), 3.24(...
Embodiment 3
[0065] Embodiment 3, the synthesis of disaccharide 5
[0066]
[0067]Disaccharide 4 (1.3 g, 1.7 mmol) was dissolved in 20 mL of anhydrous DMF, p-toluenesulfonic acid monohydrate (6.4 mg, 0.034 mmol) and 2-methoxypropene (0.31 mL, 2.5 mmol) were added with stirring. After 3 hours, the reaction was complete, and the reaction solution was concentrated under reduced pressure, and azeotropically evaporated with toluene (2×10 mL). The concentrate was separated by column chromatography (petroleum ether: ethyl acetate = 2:1) to obtain disaccharide 5 (1.2 g, 88%) as a white foamy solid. [α] D 25 -25.0°(c 0.6 CHCl 3 ).
[0068] The structural confirmation data are as follows: 1 H NMR (300MHz, CDCl 3 ): δ8.14-7.21(m, 14H, Bz-H, Phth-H), 7.06-7.03(m, 2H, Ar-H), 6.85-6.82(m, 2H, Ar-H), 5.59(dd ,1H,J 1，2 1.9Hz,J 2，3 3.6Hz, H-2-Rhap), 5.53(d, 1H, J 1.8Hz, H-1-Rhap), 5.45(d, 1H, J 8.2Hz, H-1-Glup), 5.40(t, 1H, J 9.8Hz, H-4-Rhap), 4.48 (dd, 1H, J 2，3 3.6Hz,J 3，4 9.7Hz, H-3-...
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