Name: 537-42-8|(E)-4-(3,5-Dimethoxystyryl)phenol|98%
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SKU: A181866
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1
[ 441351-31-1 ]
[ 537-42-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5767 - 5772
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 2534 - 2542
[3]Journal of Medicinal Chemistry,2003,vol. 46,p. 3546 - 3554

2
[ 848487-76-3 ]
[ 537-42-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogenchloride; In tetrahydrofuran; water; at 20℃; for 1h;	Twenty-two mL of 6 N HCl wasadded to a solution of (14) 2.5 g (8.323 mmol) in THF(25 mL) and was allowed to stir at room temperature for 1h. At the end of the reaction, the reaction mixture wastreated with water (150 mL) and extracted with EtOAc(250 mL); then, the combined organic layer was washedwith water (250 mL) and dried over Na2SO4. The crudeproduct was purified by flash column chromatography. (E)-1-(4'-Hydroxystyryl)-3,5-dimethoxybenzene (15) Whitesolid; Yield: 86 %; mp 46-48 C; 1H NMR (CDCl3,300 MHz): delta 7.39 (2H, d, J = 7.0 Hz, H-2', H-6'), 7.02(1H, d, J(trans) = 16.5 Hz, CH=(2)), 6.89 (1H, d, J(-trans) = 16.5 Hz, CH=(1)), 6.82 (2H, d, J = 7.0 Hz, H-3',H-5'), 6.64 (2H, d, J = 2.0 Hz, H-2, H-6), 6.37 (1H, t,J = 2.5 Hz, H-4), 3.82 (6H, s, 2 X O-CH3); 13C NMR(CDCl3, 75 MHz,): delta 161.5 (C, C-3, C-5), 158.9 (C, C-40),139.9 (C, C-1), 129.9 (CH, C-2', C-6'), 128.7 (CH=(2)),127.6 (C, C-1'), 126.8 (CH=(1)), 116.4 (CH, C-3', C-5'),106.3 (CH, C-2, C-6), 100.1 (CH, C-4), 56.0 (O-CH3); forC16H16O3 MS (ESI) (m/z) 257 [M +H]+.

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1292 - 1295
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 883 - 892
[3]Medicinal Chemistry Research,2016,vol. 25,p. 627 - 643

3
[ 537-42-8 ]
[ 74-88-4 ]
[ 22255-22-7 ]

Yield	Reaction Conditions	Operation in experiment
		Example 20: Synthesis of (E) -1 , 3-dimethoxy-5- (4-methoxy- styryl) benzene ARS8.; To a solution of <strong>[537-42-8]pterostilbene</strong> (lOOmg, 0.39mM) in DMF was added potassium carbonate (108mg, 0.78mM) . The reaction stirred for 30 min and methyl iodide was added (37muL,0.58mM) . The mixture was stirred for 12h at room temperature and poured into water. The mixture was extracted with ethyl acetate and the crude purified using flash chromatography eluting with ethyl acetate/hexanes (4:1) . <n="29"/>ARS8: (E) -1, 3-dimethoxy-5- (4-methoxystyryl) benzene . White solid. 1H NMR (CDCl3, 400MHz): delta 3.83 (s, 9H); 6.39 (s, IH); 6.67 (s, 2H); 6.89 (s, 2H); 6.92 (d, IH, J= 8); 7.02 (d, IH, J=8); 7.45 (d, 2H, J= 8). 13C NMR (CDCl3, 400MHz): delta 55.3 (3C), 99.6, 104.3 (2C), 114.1 (2C), 126.5, 127.8 (2C), 128.7, 129.9, 139.7, 159.4, 161.0 (2C). HRMS: CaIc for C34H36NaO6563.24096, found 563.24419 (2M+Na) .

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5767 - 5772
[2]Patent: WO2008/70872,2008,A1 .Location in patent: Page/Page column 26-27

4
[ 537-42-8 ]
C₃₂H₃₂O₇ [ No CAS ]
(E)-4-((±)-3-(3,5-dimethoxyphenyl)-5-(3,5-dimethoxystyryl)-2,3-dihydrobenzofuran-2-yl)phenol [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2007,vol. 349,p. 1497 - 1506

5
[ 353227-95-9 ]
[ 537-42-8 ]

Yield	Reaction Conditions	Operation in experiment
	With quinoline; copper; at 200℃; for 6h;Inert atmosphere;	Pterostilbene was synthesized as previously described (Joseph et al., supra). Briefly, pterostilbene was synthesized by condensation of 3,5-dimethoxybenzaldehyde and 4-hydroxyphenylacetic acid in acetic anhydride and triethylamine. The reaction mixture was heated (150 C.) under an atmosphere of nitrogen and continuously stirred. After 20 h, the reaction was stopped and cooled to room temperature, and concentrated hydrochloric acid (5 mL) was added. A precipitate formed, and this was dissolved in 50 mL of chloroform and then extracted with 10% aqueous sodium hydroxide. The aqueous extract was acidified to pH 1 with concentrated hydrochloric acid and stirred for at least 6 h, resulting in the precipitation of the intermediate product, alpha-[(3,5-dimethoxyphenyl)methylene]-4-hydroxy-(alphaZ)-benzeneacetic acid. This intermediate product was heated with 1.0 g of copper in 10 mL of quinoline (200 C., 6 h, under nitrogen). The reaction mixture was cooled to room temperature and filtered. To the filtrate was added 5 N hydrochloric acid (25 mL), which was stirred for 1 h and then extracted with chloroform. The chloroform extract containing impure pterostilbene was purified by flash chromatography on a Horizon HPFC system (Biotage, Inc., Charlottesville, Va.), using a silica gel column and the solvent system ethyl acetate:hexane (linear gradient from 15:85 to 100% ethyl acetate). Fractions containing pure pterostilbene were combined and concentrated in vacuum. Pterostilbene was recrystallized in hexane, and its structure was confirmed from its spectroscopic data (UV, mass spectrometry, and nuclear magnetic resonance spectroscopy) (FIG 1).
	With quinoline; copper; at 200℃; for 6h;Inert atmosphere;	Example 1 Pterostilbene Pterostilbene was synthesized as previously described (Joseph et al., supra). Briefly, pterostilbene was synthesized by condensation of 3,5-dimethoxybenzaldehyde and 4-hydroxyphenylacetic acid in acetic anhydride and triethylamine. The reaction mixture was heated (150 C.) under an atmosphere of nitrogen and continuously stirred. After 20 h, the reaction was stopped and cooled to room temperature, and concentrated hydrochloric acid (5 mL) was added. A precipitate formed, and this was dissolved in 50 mL of chloroform and then extracted with 10% aqueous sodium hydroxide. The aqueous extract was acidified to pH 1 with concentrated hydrochloric acid and stirred for at least 6 h, resulting in the precipitation of the intermediate product, alpha-[(3,5-dimethoxyphenyl)methylene]-4-hydroxy-(alphaZ)-benzeneacetic acid. This intermediate product was heated with 1.0 g of copper in 10 mL of quinoline (200 C., 6 h, under nitrogen). The reaction mixture was cooled to room temperature and filtered. To the filtrate was added 5 N hydrochloric acid (25 mL), which Was stirred for 1 h and then extracted with chloroform. The chloroform extract containing impure pterostilbene was purified by flash chromatography on a Horizon HPFC system (Biotage, Inc., Charlottesville, Va.), using a silica gel column and the solvent system ethyl acetate:hexane (linear gradient from 15:85 to 100% ethyl acetate). Fractions containing pure pterostilbene were combined and concentrated in vacuum. Pterostilbene was recrystallized in hexane, and its structure was confirmed from its spectroscopic data (UV, mass spectrometry, and nuclear magnetic resonance spectroscopy) (FIG. 1).

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 6967 - 6974
[2]Advanced Synthesis and Catalysis,2007,vol. 349,p. 1497 - 1506
[3]Chemistry - A European Journal,2012,vol. 18,p. 5898 - 5905
[4]Patent: US2013/296441,2013,A1 .Location in patent: Paragraph 0050
[5]Patent: US2016/67192,2016,A1 .Location in patent: Paragraph 0052

6
[ 17176-77-1 ]
[ 537-42-8 ]
[ 1028098-06-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3800 - 3808
[2]Chemistry and biodiversity,2016,vol. 13,p. 1165 - 1177

7
[ 537-42-8 ]
[ 116518-94-6 ]

Yield	Reaction Conditions	Operation in experiment
83.6%	With palladium 10% on activated carbon; hydrogen; In methanol; at 65℃; for 24h;Sealed tube;	General procedure: Substituted (E)-1,2-diphenylethene (0.200 g, 0.77 mmol) was added to a mixture of Pd/C (0.100 g, 10%) in MeOH (20 mL). The reaction mixture was recharged with H2and stirred at 65C for 24 h in a sealed tube. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10:3) to afford pure product.4-(3,5-Dimethoxyphenethyl)phenol (59).Compound22was used as starting material following the general procedure (Scheme S13) to give the desired product59(Yield 83.6%, Purity 95.6%, CAS: 116518-94-6) as a white amorphous solid.HRMS (ESI) (M-H)-m/z257.1183, calcd for C16H17O3257.1183.1H NMR (CDCl3, 500 MHz) delta: 7.19 (s, 1H), 6.99-7.02 (m, 2H), 6.72-6.75 (m, 2H), 6.33-6.33 (m, 2H), 6.31-6.32 (m, 1H), , 3.73 (s, 6H), 2.78-2.82 (m, 4H).13C NMR (CDCl3, 125 MHz) delta: 160.5, 153.9, 144.2, 133.5, 129.4, 115.2, 106.6, 97.9, 55.2, 38.3, 36.6.
	With palladium 10% on activated carbon; hydrogen; In ethanol; for 3h;	General procedure: Dihydro derivatives of compounds 7, 9, 11, 13, 15, 17, 19, 21, and 23 were prepared by hydrogenation of corresponding stilbenes. A standard protocol was followed,32 with minor modifications. Solutions of each stilbene (10mg) in absolute EtOH (5ml) were stirred under H2 for 3h in the presence of 10% Pd/C. The reaction mixtures were filtered over Celite to remove the catalyst, and evaporated to dryness. The resulting residues were purified by flash column chromatography, using a hexane/EtOAc gradient, to afford target compounds 8, 10, 12, 14, 16, 18, 20, 22, and 24, respectively, in yields of 85-95%. The spectroscopic data of compounds were in agreement with the literature, except for compound 24, for which no report was found (1H NMR spectrum is provided as Supporting information).32-41
	With hydrogen;palladium on activated charcoal; In methanol; at 20℃;	Example 21: 4- (3, 5-dimethoxyphenethyl)phenol ARSIl.; Pd/C (catalytic) was added to a solution of ptero- stilbene 2 (50mg, 0.195mM) in methanol. The mixture was left stirring overnight under H2 at room temperature. The mixture was filtered and the solvent evaporated under reduced pressure. The crude mixture was purified using flash chromatography eluting with hexanes: ethyl acetate (7:3) .ARSIl: 4- (3, 5-dimethoxyphenethyl) phenol. 1H NMR (CDCl3, 400MHz): delta 2.84 (s, 4H), 3.78 (s, 6H), 6.34-6.35 (m, 4H); 6.76 (d, 2H, J=8); 7.05 (d, 2H, J=8). 13C NMR (CDCl3, 400MHz): delta 36.7, 38.4, 55.2 (2C), 97.9, 106.6 (2C), 115.1 (2C), 129.5 (2C), 133.8, 144.2, 153.7, 160.6 (2C). HRMS: CaIc for Ci6H17O3257.11777, found 257.11889 (M-H).

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3800 - 3808
[2]European Journal of Medicinal Chemistry,2017,vol. 136,p. 382 - 392
[3]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 1276 - 1284
[4]Patent: WO2008/70872,2008,A1 .Location in patent: Page/Page column 27

8
[ 537-42-8 ]
[ 572-09-8 ]
acetic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-{4-[(E)-2-(3,5-dimethoxy-phenyl)-vinyl]-phenoxy}-2-hydroxymethyl-tetrahydro-pyran-3-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide;benzyltriethylammonium bromide; In chloroform; water; at 60℃; for 10h;	Example 24: (E) -2- (4- (3, 5-dimethoxystyryl)phenoxy) -6- (hyd- roxylmethyl)tetrahydro-2H-pyran-3,4f5-triol ARS18.; To a solution of acetobromo-alpha-D-glucose (48mg, 0.1 ImM) and benzyltriethylammonium bromide (13mg, 0.04mM) in chloroform was added a solution of <strong>[537-42-8]pterostilbene</strong> (30mg, 0.1ImM)) in 1.25 M (2.5mL) of NaOH. The mixture was stirred at 6O0C for 5h and after a second addition of lOmg of acetobromo-alpha-D-glucose and 1.0 mL of NaOH) the mixture was stirred at 6O0C for additional 5h . Ethyl acetate was added and the organic phase was washed with water. The crude mixture was purified using flash chromatography eluting with ethyl acetate/hexanes (3:2) and afforded (E) -2- (acetoxy- methyl) -6- (4- (3, 5-dimethoxystyryl) phenoxy) tetrahyd-ro-2H- pyran-3, 4, 5-triyl triacetate.

Reference： [1]Patent: WO2008/70872,2008,A1 .Location in patent: Page/Page column 29

9
[ 537-42-8 ]
[ 16420-13-6 ]
[ 1032508-01-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; In 1,4-dioxane; for 30h;Heating / reflux;	Example 25: (E) -4- (3, 5-dimethoxystyryl) benzenethiol ARS27.; A solution of <strong>[537-42-8]pterostilbene</strong> (lOOmg, 0.39mM) dimethyl thiocarbonyl chloride (58mg, 0.47mM) trietylamine (109muL,0.78mM) dimethylamino pyridine (4.7mg, 0.039mM) in dioxane(1OmL) was refluxed for 3Oh. The mixture was poured into water and extracted with ethyl acetate. The solvent was evaporated, the crude mixture was purified by column chromatography eluting with hexanes: ethyl acetate (7:3) and afforded (E) -0-4- (3, 5-dimethoxystyryl) phenyl dimethylcarb- amothioate .

Reference： [1]Journal of Agricultural and Food Chemistry,2008,vol. 56,p. 9140 - 9145
[2]Chemistry - A European Journal,2012,vol. 18,p. 5898 - 5905
[3]Patent: WO2008/70872,2008,A1 .Location in patent: Page/Page column 30

10
[ 537-42-8 ]
[ 42438-89-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 23: (E) -3- (4-hydroxystyryl) -5-methoxyphenol ARSlO.; To a solution of <strong>[537-42-8]pterostilbene</strong> (30mg, 0.1ImM) in DMF (1OmL) was added lithium thioethoxide . (135mg) . the solution was heated at 16O0C for 2 h. After cool, 15mL of HCl 0. IM was added and the mixture was extracted with ethyl acetate. The solvent was removed under reduced pressure and the crude mixture was purified using flash chromatography eluting with hexanes: ethyl acetate (3:2) . <n="31"/>ARSlO: (E) -3- (4-hydroxystyryl) -5-methoxyphenol.; 1H NMR (MeOD, 400MHz): delta 4.88 (s, 3H); 6.24 (s, IH); 6.54 (s, 2H); 6.76 (d, 2H, J=8); 6.83 (d, IH, J=I 6); 6.99 (d, IH, J=I 6); 7.35 (d, 2H, J=8) . 13C NMR (MeOD, 400MHz): delta 54.5, 100.2, 103.3, 105.5, 115.3 (2C), 125.8, 127.7 (2C), 128.5, 129.2, 140.2, 157.6, 158.4, 161.3. HRMS: CaIc for Ci5Hi3O3241.08647, found 241.08672 (M-H) .

Reference： [1]Patent: WO2008/70872,2008,A1 .Location in patent: Page/Page column 28-29

11
[ 537-42-8 ]
[ 1623-08-1 ]
[ 1028098-06-7 ]

Yield	Reaction Conditions	Operation in experiment
		Example 22: (E) -4- (3, 5-dimethoxystyryl)phenyl dihydrogen phosphate ARSl 4.; To a cold mixture (-100C) of <strong>[537-42-8]pterostilbene</strong> (200mg, 0.67mM) and N,N- (dimethylamino) pyridine (10.2mg, 0.083mM) in anhydrous acetonitrile (1OmL) was added carbon tetrachloride (323muL, 3.35mM) and DIEA (245muL, 1.4mM) . The mixture was left stirring at -100C for 30 min and dibenzyl phosphate (224muL, ImM) was added. The solution was stirred for 12h at <n="30"/>room temperature and poured into 0.5M monobasic potassium phosphate. The mixture was extracted with ethyl acetate and the organic phase dried over MgSO4. The solvent was evaporated, the crude mixture was purified by column chromatography eluting with hexanes : ethyl acetate (7:3) and afforded (E)- dibenzyl 4- (3, 5-dimethoxystyryl) phenyl phosphate.

Reference： [1]Patent: WO2008/70872,2008,A1 .Location in patent: Page/Page column 27-28

12
[ 18259-14-8 ]
[ 537-42-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In methanol; for 3h;Reflux;	General procedure: To a solution of tetrabutylammonium bromide (1.100 g, 3.33 mmol), potassium acetate (0.586 g, 3.57 mmol), and palladium acetate (0.025 g, 0.11 mmol) in DMF (20 mL) were added substituted iodobenzene (2.21 mmol) and 4-acetyloxystyrene (2.44 mmol). The reaction mixture was recharged with Argon and stirred at 80C for 5 h in a sealed tube. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10:3) to afford the intermediate substituted (E)-4-styrylphenyl acetate. To a solution of triethylamine (2.0 mL) in MeOH (5 mL) was added substituted (E)-4-styrylphenyl acetate (1.36 mmol). The reaction mixture was stirred at reflux temperaturefor 3 h. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (dichloromethane/methanol, 10:0.3) to afford pure product.

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 5668 - 5671
[2]Synthetic Communications,2013,vol. 43,p. 3217 - 3223
[3]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 5352 - 5366
[4]European Journal of Medicinal Chemistry,2017,vol. 136,p. 382 - 392

13
[ 537-42-8 ]
[ 106-95-6 ]
[ 1224713-66-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate; In acetone; at 20℃; for 5h;	To a solution of <strong>[537-42-8]pterostilbene</strong> (5 g, 0.019 mol, 1 eq) in acetone (40 mL), potassium carbonate (8 g, 0.058 mol, 3 eq), allyl bromide (2.5 g, 0.021 mol, 1.1 eq) was added at rt and stirred for 5 h at room temperature. The reaction mass was filtered and solvent was evaporated to give residue. The residue was diluted with ethyl acetate (100 mL) and washed with water and brine, dried over anhydrous sodium sulfate. The solvent was removed in vacuo and purified by silica-gel column chromatography (ethyl acetate/hexane 5:95 as eluent) to afford l-(E)-2-[4-(allyloxy)phenyl]-l-ethenyl-3,5- dimethoxybenzene as solid. Yield 4.0 g (70%).1H NuMR (DMSO, 300 Mz): delta 7.51-7.48 (d, 2H, J= 8.4 Hz), 7.21-7.16 (d, IH, J= 16 Hz), 6.96-6.91 (m, 3H), 6.71 (s, 2H), 6.36 (s, IH) ,6.0 (m, IH), 5.4-5.34 (d, 1H,17 Hz) , 5.25- 5.22 (d, IH, 10.5 Hz), 4.55-4.54 (d, 2H, 5 HzJ, 3.74 (s, 6H). LCMS: 297 (M+); HPLC: 99.87%

Reference： [1]Patent: WO2010/46926,2010,A2 .Location in patent: Page/Page column 13

14
[ 537-42-8 ]
[ 124-63-0 ]
[ 1224713-70-5 ]

Yield	Reaction Conditions	Operation in experiment
50%	With pyridine; In dichloromethane; at 0 - 20℃;	To a solution of <strong>[537-42-8]pterostilbene</strong> (5 g, 0.019 mol, 1 eq) in dichloromethane (50 mL) pyridine (4.7 g, 3 eq, 0.058 mol) was added at rt. Methane sulfonyl chloride (4.5 g, 0.039 mol, 2 eq) was added to the solution at 0 C. The solution was stirred at room temperature for 6 h. the reaction mass was poured in water and washed with IN hydrochloric acid (25 mL) and water. Evaporation of solvent gave crude product, which was triturated with hexane to obtain 4-[(£)-2-(3,5-dimethoxyphenyl)-l-ethenyl]phenyl methanesulfonate as solid. Yield 3.2 g (50%).1H NMR (CDCl3, 300 Mz): delta 7.54-7.52 (d, 2H, J= 8.7 Hz), 7.28-7.25 (d, 2H, J = 9 Hz), 7.03-7.02 (d, 2H, J =4.3Hz), 6.66-6.65 (d, 2H, J =2.2 Hz), 6.41 (m, IH), 3.82 (s, 6H), 3.15 (S, 3H). LCMS: 335 (M+); HPLC: 96.46%

Reference： [1]Patent: WO2010/46926,2010,A2 .Location in patent: Page/Page column 15

15
[ 537-42-8 ]
[ 98-59-9 ]
[ 1224713-69-2 ]

Yield	Reaction Conditions	Operation in experiment
70%	With pyridine; In dichloromethane; at 0 - 20℃;	To a solution of <strong>[537-42-8]pterostilbene</strong> (5 g, 0.019 mol, 1 eq) in dichloromethane (50 mL), pyridine (4.7g, 0.058 mol, 3 eq) was added at room temperature. /7-toluene sulfonyl chloride (3.7 g, 0.019 mol, 1 eq) was added to the solution at 0 C. The mixture was stirred at room temperature for 6 h. The reaction mass was poured in water, separated dichloromethane layer treated with IN hydrochloric acid (50 mL) and washed with water.Evaporation of solvent gave crude product, which was triturated with hexane to obtain pure product 4-[(£)-2-(3,5-dimethoxyrhohenyl)-l-ethenyl] phenyl 4-methyl-l- benzenesulfonate as solid. Yield 5.4 g (70%).

Reference： [1]Patent: WO2010/46926,2010,A2 .Location in patent: Page/Page column 14

16
[ 4530-20-5 ]
[ 537-42-8 ]
C₂₃H₂₇NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%		To a solution of 4-[(E)-2-(3, 5-Dimethoxyphenyl)-vinyl] phenol (10 g, 0.039 mol, 1 eq) in DCM (100 mL), HOBT (5.2 g, 0.039 mol, 1 eq), DCC (8 g, 0.039 mol, 1 eq), DMAP (0.47 g, 0.003 mol, 0.1 eq) were added at 0C and stirred for 30 min. BOC-Glycine (6.8 g, 0.039 mol, 1 eq) diluted in CH2Cl2 (50 mL) was added slowly to the reaction mass at 0 C. Reaction mass was slowly allowed to warm to rt and stirred for 4 h. Acetic acid (2 mL) was added and stirred for 5 min and filtered. The organic layer washed with 5% sodium carbonate (20 mL), IN HCl (20 mL). Organic solvent evaporated to give crude product, which was triturated with hexane to obtain pure desired product as solid. Yield 10 g (42%).

Reference： [1]Patent: WO2010/46926,2010,A2 .Location in patent: Page/Page column 16

17
[ 537-42-8 ]
[ 98-09-9 ]
[ 1224713-67-0 ]

Yield	Reaction Conditions	Operation in experiment
30%		To a solution of <strong>[537-42-8]pterostilbene</strong> (5 g, 0.019 mol, 1 eq) in dichloromethane (50 ml), pyridine (4.7 g, 0.058 mol, 3 eq) was added at rt and stirred for 30 min. Benzenesulfonyl chloride (3.8 g, 0.021 mol, 1.1 eq) was slowly added to reaction mass at 0 C and was allowed to rt for 2 h. Reaction mass was poured in water, separated dichloromethane layer and treated with IN hydrochloric acid (25 mL). Separated organic layer was washed with water and neutralized with 10% sodium bicarbonate solution and washed with water. Removal'of solvent gave crude product, which was triturated with hexane to obtain 4-[(E)-2-(3, 5- dimethoxyphenyl)-l-ethenyl] phenyl 1-benzenesulfonate as solid. Yield 2.3 g (30%).1H NMR (CDCl3, 300 Mz): delta 7.85-7.77 (m, 3H), 1.61-1.62 (m, 5H), 7.19-7.14 (dd, 2H, J = 13 Hz), 7.0 -6.97 (d, 2H, J= 8.7 Hzj, 6.73-6.72 (d, 2H, J= 2.2 Hz), 6.40-6.39 (t, IH, J = 2.1 Hz), 3.74(s, 6H). LCMS: 397 (M+); HPLC: 96.98%

Reference： [1]Patent: WO2010/46926,2010,A2 .Location in patent: Page/Page column 14

18
[ 537-42-8 ]
[ 105-36-2 ]
[ 1224713-71-6 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium carbonate; In acetone; at 20℃; for 3h;Reflux;	To a solution of <strong>[537-42-8]pterostilbene</strong> (10 g, 0.039 mol, 1 eq) in acetone (80 mL), potassium carbonate (16 g, 0.117 mol, 3 eq), ethylbromoacetate (7.1 g, 0.042 mol, 1.1 eq) diluted in acetone (20 mL) were added at rt. The reaction mass was refluxed for 3 h. The reaction mass was filtered and evaporated solvent to yield residue. The residue was diluted with ethyl acetate (100 mL) and washed with water and brine. Removal of organic solvent resulted crude product, which was triturated with isopropyl ether to obtain pure ethyl 2-4- [(E)-2-(3,5-dimethoxyphenyl)-l-ethenyl]phenoxyacetate as solid. Yield 7.5 g (58%).1H NMR (CDCl3, 300 Mz): delta 7.45-7.42 (d, 2H, J = 8.7 Hz), 7.00 (s, IH), 6.93-6.87 (m, 3H), 6.64-6.63 (d, 2H, J = 2.2 Hz), 6.38-6.36 (t, IH, J= 2.2 Hz), 4.63 (s, 2H), 4.28-4.24 (q, 2H), 3.82 (s, 6H), 1.32-1.27 (t, 3H, J= 7.2Hz; LCMS: 343 (M+); HPLC: 86.43%
	With potassium carbonate; In acetonitrile; at 60 - 65℃; for 8h;Inert atmosphere;	To a solution of <strong>[537-42-8]pterostilbene</strong> (3.0 g, 11.71 mmol) and anhydrous K2CO3 (2.26 g, 16.39 mmol) in CH3CN ethyl bromoacetate (1.69 mL, 15.22 mmol) was slowly added. The reaction mixture was warmed to 60-65C and stirred for 8 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Then water (60 mL) was added to the residue and the mixture was extracted with dichloromethane (40 mL×3). The combined organic phases were washed with saturated Na2CO3 aqueous solution (40 mL×3) and saturated aqueous sodium chloride (60 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness to give 2 as a light-yellow oil and the product was used in the next step without further purification.

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2018,vol. 33,p. 416 - 423
[2]Patent: WO2010/46926,2010,A2 .Location in patent: Page/Page column 15
[3]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2035 - 2039

19
[ 537-42-8 ]
[ 107-99-3 ]
[ 1224713-65-8 ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 70℃;	To a solution of <strong>[537-42-8]pterostilbene</strong> (5 g, 0.019 mol, 1 eq) in DMF (50 ml), potassium carbonate (8 g, 0.058 mol, 3 eq), N, N-Dimethyl-2-chloroethane (3 g, 0.021 mol, 1.1 eq) was added at room temperature, and then the reaction mass was heated to 70 C for Ih. Reaction mass was filtered, washed with saturated ammonium chloride and product extracted with ethyl acetate. Removal of solvent in vacuo to obtain residue, and it was purified by silica-gel column chromatography (ethyl acetate/hexane-l:3) to obtain pure title product as solid. Yield: 3.6 g (50%).1H NuMR (CDCl3, 300 Mz): delta 7.44-7.41 (d, IH, J= 8.7 Hz), 7.00-6.92 (d, IH, J= 24 Hz), 6.92-6.89 (m, 3H), 6.64-6.63 (d, 2H, J = 2.2 Hz), 6.36 (m, IH) , 4.08 (t, 2H), 3.82 (s, 6H), 2.73 (t, 2H), 2.34 (s, 6H). LCMS: 328 (M+); HPLC: 97.66%

Reference： [1]Patent: WO2010/46926,2010,A2 .Location in patent: Page/Page column 12; 13

20
[ 3240-94-6 ]
[ 537-42-8 ]
[ 936318-66-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 70℃;	To a solution of <strong>[537-42-8]pterostilbene</strong> (5 g, 0.019 mol, 1 eq) in DMF (50 ml), potassium carbonate (8 g, 0.058 mol, 3 eq) was added. 4-(2-Chloro ethane) morpholine (3.9 g, 0.020 mol, 1.1 eq) at room temperature. The reaction mass was heated to 7O0C. The reaction mass was filtered and treated with saturated ammonium chloride solution and extracted product with ethyl acetate (100 mL). Removal of solvent gave crude product, which was triturated by methanol at 00C to obtain pure title product as solid. Yield 3.6 g (50%).1H NuMR (CDCl3, 300 Mz): delta 1.44-7.41 (d, 2H, J= 8.7 Hz)5 7.00-6.92 (d, IH, J= 24 Hz), 6.87-6.86 (m, 3H), 6.64-6.63 (d, 2H, J= 2.2 Hz), 6.37-6.37 (t, IH, 2.2 Hz) , 4.10-4.12 (t, 2H, 5.7 Hz),3.82 (s, 6H), 3.72-3.73 (t, 4H, 4.7 Hz),2.80-2.82 (t, 2H, J= 5.7 Hz),2.58-2.59 (t, 4H, J= 4.7 Hzj. LCMS: 370 (M+); HPLC: 99.66%

Reference： [1]Patent: WO2010/46926,2010,A2 .Location in patent: Page/Page column 13

21
[ 15761-38-3 ]
[ 537-42-8 ]
(S)-2-tert-butoxycarbonylamino-propionic acid 4-[(E)-2-(3,5-dimethoxyphenyl)vinyl]phenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		To a solution of 4-[(E)-2-(3, 5-Dimethoxyphenyl)-vinyl] phenol (10 g, 0.039 mol, 1 eq) in dichloromethane ( 100 mL), HOBT (5.2 g, 0.039 mol, 1 eq), DCC (8 g, 0.039 mol, 1 eq), DMAP (0.47 g, 0.0039 mol, 0.1 eq) were added at O0C and stirred for 30 min. BOC- alanine (7.3 g, 0.039 mol, 1 eq) diluted in dichloromethane (50 mL) was added slowly to the reaction mass at 0 C. Reaction mass was slowly allowed to warm to rt and stirred for 4 h. Acetic acid (2 mL) was added and stirred for 5 min and filtered. The organic layer washed with 5% sodium carbonate (20 mL), IN HCl (20 mL). Organic solvent evaporated to give crude product, which was triturated with hexane to obtain pure 2-tert- Butoxycarbonylamino-propionic acid 4-[(E)-2-(3,5-dimethoxy-phenyl)-viny'l]-phenyl ester (Ala-(BOC)-OH-Pterostilbene) as solid. Yield 10 g (60%).

Reference： [1]Patent: WO2010/46926,2010,A2 .Location in patent: Page/Page column 17

22
[ 537-42-8 ]
[ 1224713-68-1 ]

Yield	Reaction Conditions	Operation in experiment
15%	With chlorosulfonic acid; triethylamine; In dichloromethane; at 0 - 20℃;	To a solution of <strong>[537-42-8]pterostilbene</strong> (5 g, 0.019 mol, 1 eq) in dichloromethane (50 mL) triethyl amine (5.9 g, 0.058 mol, 3 eq) was added at rt. Chloro sulphonic acid (2.5 g, 0.021 mol, 1.1 eq) was added to the solution at 0 C and stirred at rt for 2 h. Removal of solvent gave residue, which was purified by silica-gel column chromatography (ethyl acetate/hexane 1:1 as eluent) to obtain pure product 4-[(E)-2-(3,5-dimethoxyphenyl)-l-ethenyl]phenyl hydrogen sulfate. Yield 1.0 g (15%).1H NMR (CDCl3, 300 Mz): delta 7.49-7.46 (d, IH, J= 8.7 Hz), 7.18-7.06 (m, 4H), 6.74-6.73 (d, 2H, J= 2.2 HzJ, 6.36 (m, IH), 3.74 (s, 6H). LCMS: 337 (M+); HPLC: 98.42%

Reference： [1]Patent: WO2010/46926,2010,A2 .Location in patent: Page/Page column 14
[2]Rapid Communications in Mass Spectrometry,2010,vol. 24,p. 1770 - 1778

23
[ 537-42-8 ]
[ 130465-47-3 ]
Ser-Boc-OH-THP-pterostilbene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		To a solution of 4-[(E)-2-(3, 5-Dimethoxyphenyl)-vinyl] phenol (10 g, 0.039 mol, 1 eq) in dichloromethane ( 100 mL), HOBT (5.2 g, 0.039 mol, 1 eq), DCC (8 g, 0.039 mol, 1 eq), DMAP (0.47 g, 0.003 mol, 0.1 eq) were added at 0 C and stirred for 30 min. BOC- ser-(THP)-OH (11.8 g, 0.039 mol, 1 eq) diluted in 50 ml of dichloromethane was added slowly to the reaction mass at 0 C. Reaction mass was slowly allowed to warm to rt and stirred for 4 h. Acetic acid (2 mL) was added and stirred for 5 min and filtered. The organic layer washed with 5% sodium carbonate (20 mL), IN HCl (20 mL). Organic solvent was evaporated to give crude product, which was triturated with hexane to obtain pure desired product as solid. Yield 13.0 g (60%).

Reference： [1]Patent: WO2010/46926,2010,A2 .Location in patent: Page/Page column 18

24
(E)-4'-benzyloxy-3,5-dimethoxystilbene [ No CAS ]
[ 537-42-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With hydrogen; In dichloromethane; at 20℃; under 3750.38 Torr; for 5h;	3,5-dimethoxy-4'-benzyloxyphenyl stilbene 17.38,Dissolved in 601 ^ 012 (: 12, then add 5.198Pd load of 5% of the catalyst RS001, 0.5MPa pressure into the hydrogen, stirring at room temperature for 5h, after the end of the reaction,The filter recovery catalyst RS001,The filtrate was steamed to recover the reaction solvent to obtain crude product. The crude product was recrystallized from ethanol to give 11,188 of pterostilbene and 87% yield.

Reference： [1]Patent: CN106995364,2017,A .Location in patent: Paragraph 0031; 0032
[2]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 971 - 975

25
[ 25245-27-6 ]
[ 2628-17-3 ]
[ 537-42-8 ]

Yield	Reaction Conditions	Operation in experiment
83.4%		To a 25 mL single-necked flask was added 3,5-dimethoxyiodobenzene (5 mmol)And pd (oAc) 2 (1.0 mol%) / Eosin Y (1.5 mol%)Dissolved in 6 mL DMF (DMF: H2O = 5: 1) aqueous solution,Then, p-hydroxystyrene (5.3 mmol) was slowly added dropwise,The reaction was stirred at room temperature for about 15 h,TLC detection reaction ends. The reaction product was washed with water, separated, dried,Filtered, concentrated, recrystallized from ethyl acetate,To obtain a white crystal, i.e. derivative 6a. the yield of 83.4%.
55%	With triethanolamine; palladium diacetate; at 100℃; for 24h;Inert atmosphere;	General procedure: A mixture of the styrene (3 mmol), the halogenated benzene (3 mmol), triethanolamine (3 mmol) and Pd(II) acetate (0.03 g) was stirred under argon at 100 C for 24 h. The reaction was cooled to 25 C, quenched by the addition of dil. aq. hydrochloric acid (2 N, 10 ml), and extracted with ether (3 × 100 ml). The organic phases were dried (Na2SO4), the solvents evaporated, and the crude product subjected to chromatography (silica gel, hexane/ethyl acetate mixtures).
55%	With triethanolamine; palladium diacetate; at 100℃; for 24h;Inert atmosphere;	General procedure: A mixture of the styrene (3 mmol), the halogenated benzene (3 mmol), triethanolamine (3 mmol) and Pd (II) acetate (0.03 g) was stirred under argon at 100 C for 24 h. The reaction was cooled to 25 C, quenched by the addition of dil. aq. hydrochloric acid (2 N, 10 ml), and extracted with ether (3 × 100 ml). The organic phases were dried (Na2SO4), the solvents evaporated, and the crude product was subjected to chromatography (silica gel, hexane/ethyl acetate mixtures).

Reference： [1]Patent: CN106588582,2017,A .Location in patent: Paragraph 0017; 0018
[2]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 5155 - 5166
[3]European Journal of Medicinal Chemistry,2012,vol. 54,p. 669 - 678

26
C₁₉H₂₄O₃Si [ No CAS ]
[ 537-42-8 ]
[ 441351-32-2 ]

Yield	Reaction Conditions	Operation in experiment
	With water; In tetrahydrofuran; at 20℃; for 1h;Inert atmosphere; Cooling with ice;	General procedure: 3.5.1. (E)-4-Hydroxy-4'-methoxystilbene (4b). Under argon atmosphere, butyllithium (1.6 M, 20 mL, 32 mmol) was slowly added to a solution of (4-methoxybenzyl)triphenylphosphonium bromide (13.8 g, 33 mmol) in THF (70 mL) at -78 C. The resulting reddish solution was allowed to warm at room temperature. Freshly distilled 4-trimethylsilyloxybenzaldehyde (6.37 g, 33 mmol) was added dropwise and the reaction mixture was stirred for a night, diluted with ice-cold water (200 mL) and stirred for an additional hour. The aqueous layer was extracted with ethylacetate; the combined organic layers were washed with water and dried. After evaporating the solvent, 6.4 g (86%) of a crude mixture of isomers Z and E was isolated as brown oil. Pure isomer E, which was crystallized from ethanol (2.4 g, 32%).

Reference： [1]Tetrahedron,2012,vol. 68,p. 3899 - 3907

27
[ 1012-12-0 ]
[ 537-42-8 ]
[ 441351-32-2 ]

Reference： [1]Tetrahedron,2012,vol. 68,p. 3899 - 3907

28
[ 40243-87-6 ]
4-hydroxybenzenediazonium tetrafluoroborate [ No CAS ]
[ 537-42-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 3674 - 3691
[2]Organic Letters,2019,vol. 21,p. 8389 - 8394

29
[ 7311-34-4 ]
[ 109103-16-4 ]
tripropylphosphine hydrohalide [ No CAS ]
[ 537-42-8 ]

Yield	Reaction Conditions	Operation in experiment
		To the protected benzyl alcohol 11 (2.0 g, 7.2 mmol, 1 equiv.) wasadded tripropylphosphine hydrobromide (1.7 g, 7.2 mmol, 1 equiv.) andacetonitrile (0.5 mL). The reaction was then heated to 100 C for 8 h. Thetitle compound crystallized slowly over four days. To a round-bottomed flask was added phosphoniumsalt 12a (1.65 g, 3.3 mmol, 1.1equiv.), aldehyde 8 (0.500 g, 3mmol, 1.0 equiv.) and lithium hydroxide (0.240 g, 9.9 mmol, 3 equiv.). Water (3mL) was added to make a 1 M solutionand the reaction heated to 90 C for 12 h with vigorous stirring. Upon coolingto room temperature the mixture was acidified to a pH of 2 with 1 N HCl and stirred vigorously for 10 minutes.The crude product was extracted with EtOAc (2 x 5 mL) and concentrated underreduced pressure prior to filtration through silica. This crude product canthen be either column chromatographed over silica gel or recrystallized fromEtOH/H2O. Yield 89%, Colourless solid; TLC (EtOAc/Hexane, 2:3 v/v):Rf = 0.39; 1H-NMR [CDCl3, 600 MHz] delta: 7.40 (d,J = 8.5 Hz, 2H), 7.03 (d, J = 16.3 Hz, 1H), 6.90 (d, J = 16.3 Hz, 1H), 6.84 (d, J = 8.7 Hz, 2H), 6.66 (d, J = 2.3 Hz, 2H), 6.40 (t, J = 2.0 Hz, 1H), 5.52 (bs, 1H), 3.84 (s,6H); 13C-NMR [CDCl3, 150 MHz] delta: 161.1, 155.5, 139.8,130.2, 128.8, 128.1, 126.8 115.8, 104.5, 99.8, 55.5.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 6303 - 6306

30
[ 537-42-8 ]
[ 5538-51-2 ]
[ 1511857-25-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine; In dichloromethane; at 0 - 20℃; for 2h;	Di-methylated resveratrol (<strong>[537-42-8]pterostilbene</strong>; Pt) was reacted with 1.2 equivalents of acetylsalicyloyl chloride under basic conditions to generate <strong>[537-42-8]pterostilbene</strong> aspirinate (PAS; yield: 96%). The structure of PAS was determined by 1H, 13C, and 2D (HMQC and HMBC) NMR and MS analysis. PAS: white solid; 1H NMR (700 MHz, CDCl3) delta 6.66 (2H, t, J=2.0 Hz, H-2/6), 6.39 (1H, t, J=2.0 Hz, H-4), 6.99 (1H, d, J=16.1 Hz, H-7), 7.07 (1H, d, J=16.1 Hz, H-8), 7.53 (2H, d, J=8.4 Hz, H-10/14), 7.16 (2H, d, J=8.4 Hz, H-11/13), 7.17 (1H, d, J=8.0 Hz, H-4?), 7.62 (1H, dt, J=8.0, 1.4 Hz, H-5?), 7.37 (1H, t, J=8.0 Hz, H-6?), 8.21 (1H, dd, J=8.0, 1.4 Hz, H-7?), 2.30 (3H, s, CH3C?O), and 3.81 (6H, s, OMe-3/5); 13C NMR (175 MHz, CDCl3) delta 139.2 (s, C-1), 104.6 (d, C-2/6), 161.0 (s, C-3/5), 100.1 (d, C-4), 129.1 (d, C-7), 128.1 (d, C-8), 135.3 (s, C-9), 127.7 (d, C-10/14), 121.9 (d, C-11/13), 150.0 (s, C-12), 163.0 (s, C-1?), 122.5 (s, C-2?), 151.2 (s, C-3?), 124.1 (d, C-4?), 134.7 (d, C-5?), 126.3 (d, C-6?), 132.3 (d, C-7?), 169.8 (s, CH3CC?O), 21.1 (q, CH3C?O), and 55.4 (q, OMe-3/5); positive APCIMS, m/z 419 [M+H]+.

Reference： [1]Patent: US2013/338120,2013,A1 .Location in patent: Paragraph 0180; 0181; 0182
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 6494 - 6506

31
[ 878-00-2 ]
[ 1532557-35-9 ]
[ 18259-14-8 ]
[ 537-42-8 ]

Yield	Reaction Conditions	Operation in experiment
53%; 19%		LiHMDS (17.1mL of 1.0M solution in THF, 10.3 mmol) was added to a solutionof sulfone 5 (3.0 g, 8.5 mmol) in anhydrous THF (30 mL) at 78 C and stirredfor an additional 30 min at the same temperature. To this cold solution, aldehyde 7a(1.75 g, 10.63 mmol) in THF (20 mL) was added and stirring continued at 78 C.After 3 h, the mixture was quenched with saturated NH4Cl solution and extractedwith EtOAc (325 mL). The combined organic layers were washed with water andsaturated NaCl, dried over anhydrous Na2SO4, and concentrated under reducedpressure to yield the crude product. The residue was purified by silica-gel columnchromatography using EtOAc (5-20%) in hexanes to give 4-acetyl pterostilbene(1.35 g, 53% yield) and pterostilbene (0.42 g, 19% yield).

Reference： [1]Synthetic Communications,2013,vol. 43,p. 3217 - 3223

32
[ 537-42-8 ]
C₁₁H₁₈O₆ [ No CAS ]
pterostilbene D-ribonic acid diacetonide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 18h;	To a solution of compound 14-4 (2.2 g, 8.6 mmol) in DMF, compound 14-3 (3.19 g. 13.0 mmol), dicyclohexylcarbodiimide (2.96 g, 14.3 mmol) and 4-dimethylaminopyridine (71.4 mg, 0.6 mmol) were added stepwisely and then stirred at room temperature for 18 hours. The reaction mixture was quenched with water and extracted with methylene chloride. The organic layer was washed with brine, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to provide compound 14-5 (3.0 g, 6.2 mmol) in 72% yield. [0088] 1H NMR (500 MHz, DMSO-d6): delta: 1.29 (s, 3H), 1.35 (s, 3H), 1.36 (s, 3H),1.47 (s, 3H), 3.78 (s, 6H), 3.86 (m, 1H), 4.12 (m, 2H), 4.39 (m, 1H), 5.04 (d, 1H), 6.42 (t, 1H), 6.78 (d, 2H), 7.19 (m, 3H), 7.27 (d, 1H), 7.66 (d, 2H). MS: 485.0 (M+1). Melting point of compound 14-5:107.0-109.0 C.

Reference： [1]Patent: EP2786981,2014,A1 .Location in patent: Paragraph 0084; 0087-0088

33
[ 331810-11-8 ]
[ 537-42-8 ]
C₂₄H₂₈O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine; In dichloromethane; at 20℃; for 1h;	General procedure: The general procedure is illustrated immediately below with compound12 as a specific example. To a solution of compound 7 (1.100 g,4.30 mmol) in CH2Cl2 (10 mL) were slowly added 2,2,5-trimethyl-1,3-dioxane-5-carbonyl chloride (913 mg, 4.70 mmol) and triethylamine(0.9 mL, 6.50 mmol). The resulting mixture was stirred at rt for 1.0 h.Then saturated NH4Cl solution (3 mL) and water (5 mL) were added toquench the reaction. The aqueous layer was separated and extractedwith CH2Cl2 (2×10 mL). The combined organic extracts were washedwith brine, dried over Na2SO4, filtered and concentrated to give thecrude residue, which was purified by flash chromatography on silicalgel to provide compound 7 (1.503 g, 85% yield). To a stirred solution ofcompound 7 (0.928 g, 2.40 mmol) in THF (15 mL) was added 12 N HCl(0.2 mL) at rt. The reaction mixture was stirred at the same temperaturefor 1 h and then concentrated to give the crude product, which was thenpurified by flash chromatography on silical gel (EtOAc:n-hexane=2:1)to give compound 12 (0.752 g, 90% yield) as a white solid.
	With triethylamine; In dichloromethane; at 20℃; for 1h;	To a solution of compound 11-1 (1.1 g, 4.3 mmol) in methylene chloride (10 mL), 2,2,5-trimethyl-1,3-dioxane-5-carbonyl chloride (913 mg, 4.7 mmol) and triethylamine (0.9 mL, 6.5 mmol) were slowly added and then stirred at room temperature for 1.0 hour. The reaction mixture was quenched with water and extracted with methylene chloride. The organic layer was washed with brine, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to provide compound 11-2.

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3909 - 3916
[2]Patent: EP2786981,2014,A1 .Location in patent: Paragraph 0072-0073

34
[ 537-42-8 ]
[ 598-21-0 ]
(E)-4'-(3,5-Dimethoxystyryl)phenyl 2-bromoacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine; In dichloromethane; at 0℃;	Bromoacetyl bromide (3.901mmol, 1.0 equiv) was added drop wise over 5 min to asolution of amine (9) or phenol (15) 1 g (3.885 mmol, 1.0equiv) and triethylamine (4.291 mmol, 1.1 equiv) indichloromethane (50 mL), at 0 C. The reaction mixturewas stirred at 0 C for 20 min to 1 h, diluted withdichloromethane (50 mL), washed with saturated NH4Cl (3X 30 mL), dried (Na2SO4), and concentrated in vacuo toafford the crude product. The crude product was purified byflash column chromatography, to yield pure (E)-2-bromo-N-(4'-(3,5-dimethoxystyryl)phenyl)acetamide or (E)-4'-(3,5-dimethoxystyryl)phenyl 2-bromoacetate.

Reference： [1]Medicinal Chemistry Research,2016,vol. 25,p. 627 - 643

35
[ 537-42-8 ]
[ 621-82-9 ]
4-(3,5-dimethoxystyryl)phenyl cinnamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃;	The caffic acid derivitives (1mmol), HATU (1.2mmol) and N,N-diisopropylethylamine (2mmol) were dissolved in dichloromethane and stirred at room temperature for 30min. Compound 11 (1mmol) was then added to the solution, and stirred overnight. The reaction mixture was extracted with dichloromethane. The organic layer was washed with diluted hydrochloric acid, saturated sodium bicarbonate solution and brine. Then it was dried with anhydrous magnesium sulfate, and the solvent was evaporated in vacuum to give the crude product, which was purified by chromatography on silica gel. 4.1.6.1 4-(3,5-dimethoxystyryl)phenyl cinnamate (12a) Yield 93%, white solid, m.p. 138-139C; IR (KBr) nu 3432, 1731, 1633, 1594, 1311, 1145, 840cm-1; 1H NMR (500MHz, DMSO) delta 7.88 (d, J=16.0Hz, 1H), 7.85-7.79 (m, 2H), 7.67 (d, J=8.6Hz, 2H), 7.50-7.45 (m, 3H), 7.31 (d, J=16.4Hz, 1H), 7.23 (d, J=8.5Hz, 2H), 7.18 (d, J=16.4Hz, 1H), 6.90 (d, J=16.0Hz, 1H), 6.79 (d, J=2.0Hz, 2H), 6.43 (t, J=2.0Hz, 1H), 3.79 (s, 6H); 13C NMR (126MHz, DMSO) delta 164.84, 160.66, 149.91, 146.45, 138.98, 134.68, 133.82, 128.96, 128.60, 127.97, 127.46, 122.04, 117.14, 104.52, 99.95, 55.19; HRMS (ESI) m/z 387.1587 [M+H]+ (calcd for 387.1591, C25H23O4).

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 124,p. 1006 - 1018

36
[ 16642-92-5 ]
[ 537-42-8 ]
(E)-4-(3,5-dimethoxystyryl)phenyl 3-(4-(trifluoromethyl)phenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃;	General procedure: The caffic acid derivitives (1mmol), HATU (1.2mmol) and N,N-diisopropylethylamine (2mmol) were dissolved in dichloromethane and stirred at room temperature for 30min. Compound 11 (1mmol) was then added to the solution, and stirred overnight. The reaction mixture was extracted with dichloromethane. The organic layer was washed with diluted hydrochloric acid, saturated sodium bicarbonate solution and brine. Then it was dried with anhydrous magnesium sulfate, and the solvent was evaporated in vacuum to give the crude product, which was purified by chromatography on silica gel.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 124,p. 1006 - 1018

37
[ 619-89-6 ]
[ 537-42-8 ]
(E)-4-(3,5-dimethoxystyryl)phenyl 3-(4-nitrophenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃;	General procedure: The caffic acid derivitives (1mmol), HATU (1.2mmol) and N,N-diisopropylethylamine (2mmol) were dissolved in dichloromethane and stirred at room temperature for 30min. Compound 11 (1mmol) was then added to the solution, and stirred overnight. The reaction mixture was extracted with dichloromethane. The organic layer was washed with diluted hydrochloric acid, saturated sodium bicarbonate solution and brine. Then it was dried with anhydrous magnesium sulfate, and the solvent was evaporated in vacuum to give the crude product, which was purified by chromatography on silica gel.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 124,p. 1006 - 1018

38
[ 459-32-5 ]
[ 537-42-8 ]
(E)-4-(3,5-dimethoxystyryl)phenyl 3-(4-fluorophenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃;	General procedure: The caffic acid derivitives (1mmol), HATU (1.2mmol) and N,N-diisopropylethylamine (2mmol) were dissolved in dichloromethane and stirred at room temperature for 30min. Compound 11 (1mmol) was then added to the solution, and stirred overnight. The reaction mixture was extracted with dichloromethane. The organic layer was washed with diluted hydrochloric acid, saturated sodium bicarbonate solution and brine. Then it was dried with anhydrous magnesium sulfate, and the solvent was evaporated in vacuum to give the crude product, which was purified by chromatography on silica gel.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 124,p. 1006 - 1018

39
[ 90-50-6 ]
[ 537-42-8 ]
(E)-4-(3,5-dimethoxystyryl)phenyl 3-(3,4,5-trimethoxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃;	General procedure: The caffic acid derivitives (1mmol), HATU (1.2mmol) and N,N-diisopropylethylamine (2mmol) were dissolved in dichloromethane and stirred at room temperature for 30min. Compound 11 (1mmol) was then added to the solution, and stirred overnight. The reaction mixture was extracted with dichloromethane. The organic layer was washed with diluted hydrochloric acid, saturated sodium bicarbonate solution and brine. Then it was dried with anhydrous magnesium sulfate, and the solvent was evaporated in vacuum to give the crude product, which was purified by chromatography on silica gel.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 124,p. 1006 - 1018

40
[ 537-42-8 ]
(trans)-4-[2-(3,5-dimethoxyphenyl)ethenyl]-1,2-benzenediol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.4%	With ascorbic acid; In aq. phosphate buffer; dimethyl sulfoxide; at 25℃;pH 6.0;	A substrate solution containing 20.0mM PS, 40.0mM L-ascorbicacid and 50% (v/v) DMSO (for pre-dissolving PS) was prepared inphosphate buffer (50 mM, pH 6.0). The reaction was conducted byadding 10.0 mg CLEAs to 2.0 mL of the substrate solution, which wasplaced in a capped test tube in a shaking incubator with agitation of220 rpm at 25 C. At intervals, a 20 muL sample was taken and 20 timesdiluted with 50% (v/v) acetonitrile aqueous solution before beingsubjected to HPLC analysis as described below.
2.5 g	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20℃;Green chemistry;	To a solution of <strong>[537-42-8]pterostilbene</strong> (iO g) in DMSO (50 ml) 113X was added (i .2 eq). The reaction mixture was stirred at room temperature and monitored by TEd. When the substrates disappeared, reaction mixture quenched with waterand sodium dithionite solution. Product extracted with ethylacetate. The organic phases were washed with a solution ofsodium bicarbonate and dried on sodium sulfate. The organic layer was evaporated under reduced pressure obtaining crude product which was purified by column chromatography on silica gel (Yield: 2.5 g). It may be noted that the orthohydroxylation of <strong>[537-42-8]pterostilbene</strong> using 113X followed byin situ sodium dithionite reduction resulted in only 25% yield of 3?-hydroxy<strong>[537-42-8]pterostilbene</strong>. Nevertheless, the methodwas technically advantageous being a single step, greenchemistry based synthesis.The aforesaid examples are provided to enable one skilled in the art to practice the invention. The examples merely illustrate the general process of the invention. However, theincluded examples are not intended in any way to limit thescope of the present invention.

Reference： [1]Process Biochemistry,2018,vol. 70,p. 90 - 97
[2]Patent: US9458075,2016,B1 .Location in patent: Page/Page column 4
[3]Molecules,2019,vol. 24
[4]Biocatalysis and Biotransformation,2020

41
[ 50-00-0 ]
[ 537-42-8 ]
3'-formylpterostilbene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90 g	With triethylamine; magnesium chloride; In acetonitrile; at 20℃;Reflux;	Example 1 Preparation of 3'-Formyl Pterostilbene To a solution of <strong>[537-42-8]pterostilbene</strong> (100 g, 0.3906 mol, 1 eq) in acetonitrile (1.0 liter), paraformaldehyde (94 g, 3.125 mol, 8 eq), triethylamine (163 ml, 1.1718 mol, 3 eq) and anhydrous magnesium chloride (111 g, 1.1718 mol, 3 eq) were added at room temperature. The solution was stirred for 5-6 hours at reflux temperature and monitored by TLC. When the substrates disappeared, water was added and acidified with dil HCl. Reaction mixtures were extracted with dichloromethane. Organic phases were washed with water and then dried on sodium sulfate. The organic solvent was evaporated under reduced pressure obtaining crude product, which was stirred with isopropyl alcohol at 0 C. to obtain pure product as solid (Yield: 90 g).

Reference： [1]Patent: US9458075,2016,B1 .Location in patent: Page/Page column 4

42
[ 537-42-8 ]
di-(triphenylmethoxy)-phosphoryl chloride [ No CAS ]
C₅₄H₄₅O₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With dmap; N-ethyl-N,N-diisopropylamine; In chloroform; at 20℃; for 0.5h;Inert atmosphere;	Under the protection of nitrogen, 2 · 56g (0. Olmol)4'-dimethylaminopyridine 0. 068 (0 0005piomicron1)And diisopropylethylamine 1. 42 g (0.1 l mol)Dissolved in 20mlIn chloroform,At 20 C,DripDi- (triphenylmethoxy) -phosphoryl chloride6. 61g (0. Ollmol)And 10 ml of trichloromethane.After completion of the dropwise addition, the temperature stirring reaction was maintained,With thin layer chromatography to monitor the reaction process, to the disappearance of raw materials,The reaction time was 0. 5 hours,The reaction solution was poured into 50 ml of ice water. The organic layer was separated and the aqueous layer was extracted again with 20 ml of trichloromethane. The organic layers were combined, washed with water, dried and evaporated to give a yield of 89% Oily Styrofoam - di- (triphenylmethoxy) -phosphate 7. 92 g,And put it into 50ml has been pre-drying dry hydrogen chloride to saturated methanol,The reaction was stirred at room temperature for 24 hours,The solvent was evaporated under reduced pressure and the residue was dissolved in 50 ml of dichloromethane,Washed to neutral, anhydrous sodium sulfate dry, evaporated,The residue was dissolved in 25 ml of methanol,NaOH-methanol solution was added dropwise to pH 8 to 10 with stirring,Stirring for 1 hour,Slowly dropping acetone 200ml,Filtered, acetone washed with solid, dried under reduced pressure,A white powdery product of 2. 46 g was obtained in a yield of 69.5%.

Reference： [1]Patent: CN103408591,2016,B .Location in patent: Paragraph 0029-0030

43
[ 537-42-8 ]
[ 538-37-4 ]
[ 1028098-06-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 1h;Inert atmosphere;	Under nitrogen protection, A mixture of 2.65 mol (0. Olmol), 4'-dimethylaminopyridine 0. 06g (0. 0005piomicron1)And diisopropylethylamine 1. 42 g (0. 01 lmol) was dissolved in 20 ml of dichloromethane,At 20 C,DroppingDi- (benzyloxy) -phosphoryl chloride2. 92 g (0. Ollmol)And 10mll of dichloromethane.Maintaining the temperature stirring reaction, monitoring the reaction process with thin layer chromatography,To the raw material point disappears, the reaction time is 1 hour,The reaction solution was poured into 50 ml of ice water and the organic layer was separated.The aqueous layer was extracted again with 20 ml of dichloromethane,The organic layers were combined, washed with water, dried,Evaporated to yield a yield of 96%Oily Safflower - Bis (Benzyloxy) _ Phosphate 4. 5g,Put it in 25 ml of methanol, add 10% Pd / C0. 04g,The reaction was quenched with hydrogen at room temperature for 24 hours at room temperature,The catalyst was removed by filtration,NaOH-methanol solution was added dropwise to pH 8 to 10 with stirring, stirred for 1 hour,Slowly dropping acetone 200ml,Filtered, acetone washed with solid, dried under reduced pressure,A white powdery product of 2. 84 g, yield 80.5%

Reference： [1]Patent: CN103408591,2016,B .Location in patent: Paragraph 0031-0032

44
[ 56119-60-9 ]
[ 537-42-8 ]
C₂₄H₃₃O₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h;Inert atmosphere;	Under nitrogen protection, the <strong>[537-42-8]pterostilbene</strong> 2·56g (0.01mol), 4'-dimethylaminopyridine 0·06g (0. 0005 momicronl) And diisopropylethylamine 1. 42 g (0. O11mol) Dissolved in 20 ml of methylene chloride,At 20 C,A solution of bis (t-butoxy)-phosphoryl chloride was added dropwise2.51 g (0.011 mol) and 10 ml of dichloromethane.After completion of the dropwise addition, the temperature stirring reaction was maintained,The reaction process was monitored by thin layer chromatography,To the disappearance of raw materials,The reaction time was 0. 5 hours,The reaction solution was poured into 50 ml of ice water, the organic layer was separated, the aqueous layer was extracted again with 20 ml of dichloromethane,The organic layers were combined, washed with water, dried and evaporated to a yield of 94% Oil <strong>[537-42-8]pterostilbene</strong>-di-(t-butoxy)-phosphate 4. 07g,And put it into 50ml Has been pre-drying dry hydrogen chloride to saturated methanol,The reaction was stirred at room temperature for 24 hours, Vacuum drying solvent,The residue was dissolved in 50 ml of dichloromethane,Washed to neutral,Dried over anhydrous sodium sulfate,Evaporated,The residue was dissolved in 25 ml of methanol,The addition of NaOH-Methanol solution to pH 8 to 10,Stirring for 1 hour,Slowly dropping acetone 200ml,filter,Acetone washed solids, Decompression drying,A white powdery product, 2.95 g, yield 82.7%.

Reference： [1]Patent: CN103408591,2016,B .Location in patent: Paragraph 0025-0026

45
[ 874201-26-0 ]
[ 537-42-8 ]
C₂₂H₂₃N₂O₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 30℃; for 0.8h;Inert atmosphere;	Under nitrogen protection,A mixture of 2.65 mol (0 Olmoi)4'-dimethylaminopyridine 0. 06g (0. 0005piomicron1)And diisopropylethylamine 1.428 (0. 01 lmol) were dissolved in 20 ml of dichloromethane,At 30 C,Drip(2-cyanoethoxy) -phosphoryl chloride2.45 g (0.011 mol) and 10 ml of dichloromethane.After the dropwise addition, the reaction was maintained at this temperature, the reaction progress was monitored by thin layer chromatography,To the disappearance of raw materials,The reaction time was 0. 8 hours,The reaction solution was poured into 50 ml of ice water, and the organic layer was separated,The aqueous layer was extracted again with 20 ml of dichloromethane and the combined organic layers were washed with water, dried and evaporated to give a yield of 93%(2-cyanoethoxy) -phosphate 4. 45 g,Put it into 25ml methanol,NaOH-methanol solution was added dropwise to pH 8 to 10 with stirring, stirred for 1 hour,Slowly add 200 ml of acetone, filter, acetone wash the solid, Dried under reduced pressure to give 2.83 g of product as a white powder, yield 78%.

Reference： [1]Patent: CN103408591,2016,B .Location in patent: Paragraph 0027-0028

46
[ 537-42-8 ]
[ 952585-00-1 ]
[ 50450-35-6 ]

Yield	Reaction Conditions	Operation in experiment
	With Phytolacca americana glucosyltransferase; In aq. phosphate buffer; at 35℃; for 24h;pH 7.2;Enzymatic reaction;	General procedure: Glucosylation reactions were performed at 35 C for 24 h in 5 mL of 50 mM potassium phosphate buffer (pH 7.2) supplemented with 50 muM substrate, 100 muM UDP-glucose, and 5 muM enzyme. The incubation was stopped by adding 1.5% trifluoroacetic acid; and the reaction mixture was analyzed by high performance liquid chromatography (HPLC). The reaction mixture was extracted with n-BuOH. The n-BuOH fraction was concentrated by evaporation and the residue was dissolved in water. The water fraction was applied to Diaion HP20, washed with water, and eluted with methanol. The methanol solution was subjected to preparative HPLC.

Reference： [1]Bioscience, Biotechnology and Biochemistry,2017,vol. 81,p. 226 - 230

47
[ 537-42-8 ]
(Z)-3-((10-(((4-nitrophenoxy)carbonyl)amino)decanoyl)oxy)propane-1,2-diyl dioleate [ No CAS ]
(Z)-3-((10-(((4-((E)-3,5-dimethoxystyryl)phenoxy)carbonyl)amino)decanoyl)oxy)propane-1,2-diyl dioleate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With dmap; In tetrahydrofuran; at 50℃; for 18h;	Pterostilbene (0.28g, 1.1mmol, 3.0 equiv.) and DMAP (0.13g, 1.1mmol, 3.0 equiv.) were added to a solution of 10 (0.35g, 0.36mmol, 1.0 equiv.) in HPLC grade THF (8.0mL) and the resulting solution was stirred at 50C for 18h. The reaction mixture was diluted with DCM (25mL) and washed with HCl 0.5M (50mL). The aqueous layer was extracted with DCM (2×25mL) and the combined organic layers were dried over MgSO4. The solvent was removed under reduced pressure and the oily residue was purified twice by flash chromatography (1st: petroleum ether/acetone 8:2, Rf=0.40; 2nd: DCM/acetone 99:1) to afford 0.17g, 0.16mmol of Type-1 (43% yield) as a colourless oil. 1H NMR (300MHz, CDCl3) delta 7.47 (d, J=8.4Hz, 2H, H-2? and H-6?), 7.16-7.01 (m, 3H, Ar-CH=CH-Ar, H-3? and H-5?), 6.96 (d, J=16.2Hz, 1H, Ar-CH=CH-Ar), 6.66 (m, 2H, H-2 and H-6), 6.41-6.37 (m, 1H, H-4), 5.41-5.22 (m, 5H, 2×-CH=CH- and -CH2-CH-CH2-), 5.12-5.04 (m, 1H, -NH-), 4.30 (dd, J=11.9, 4.2Hz, 2H, -CH2-CH-CH2-), 4.14 (dd, J=11.9, 5.9Hz, 2H, -CH2-CH-CH2-), 3.82 (s, 6H, 2×-OCH3), 3.30-3.20 (m, 2H, -CH2-NH-), 2.36-2.26 (m, 6H, 3×-CH2-COO-), 2.07-1.94 (m, 8H, 2×-CH2-CH=CH-CH2-), 1.68-1.51 (m, 8H, -CH2-CH2-NH- and 3×-CH2-CH2-COO-), 1.40-1.18 (m, 50H, 25×-CH2-), 0.92-0.83 (m, 6H, 2×-CH3). 13C NMR (75MHz, CDCl3) delta 173.4, 173.3, 172.9, 161.1, 154.5, 150.8, 139.4, 134.4, 130.1, 130.1, 129.8, 129.8, 128.6, 128.5, 127.5, 121.9, 104.7, 100.1, 69.0, 62.2, 55.5, 41.4, 34.3, 34.1, 34.1, 32.0, 29.9, 29.8, 29.8, 29.6, 29.4, 29.3, 29.3, 29.2, 29.2, 29.2, 29.2, 27.3, 27.3, 26.8, 25.0, 25.0, 24.9, 22.8, 14.2. ESI-MS (ESI+): 1073m/z [M+H]+, 1090m/z [M+NH4]+, 1095m/z [M+Na]+, 1111m/z [M+K]+. Purity ?95% (HPLC).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 135,p. 77 - 88

48
[ 537-42-8 ]
(Z)-2-((10-(((4-nitrophenoxy)carbonyl)amino)decanoyl)oxy)propane-1,3-diyl dioleate [ No CAS ]
(Z)-2-((10-(((4-((E)-3,5-dimethoxystyryl)phenoxy)carbonyl)amino)decanoyl)oxy)propane-1,3-diyl dioleate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With dmap; In tetrahydrofuran; at 50℃; for 18h;	Pterostilbene (0.30g, 1.2mmol, 3.0 equiv.) and DMAP (0.14g, 1.2mmol, 3.0 equiv.) were added to a solution of 15 (0.37g, 0.39mmol, 1.0 equiv.) in HPLC-grade THF (8.0mL) and the resulting solution was stirred at 50C for 18h. The reaction mixture was diluted with DCM (25mL) and washed with HCl 0.5M (50mL). The aqueous layer was extracted with DCM (2×25mL) and the combined organic layers were dried over MgSO4. The solvent was removed under reduced pressure and the oily residue was purified two times by flash chromatography (1st: petroleum ether/acetone 8:2, Rf=0.39; 2nd: DCM/acetone 99:1) to afford 0.19g, 0.18mmol of Type-2 (46% yield) as a white solid. 1H NMR (300MHz, CDCl3) delta 7.47 (d, J=8.5Hz, 2H, H-2? and H-6?), 7.17-7.01 (m, 3H, Ar-CH=CH-Ar, H-3? and H-5?), 6.96 (d, J=16.2Hz, 1H, Ar-CH=CH-Ar), 6.66 (d, J=2.1Hz, 2H, H-2 and H-6), 6.39 (t, J=2.0Hz, 1H, H-4), 5.42-5.21 (m, 5H, 2×-CH=CH- and -CH2-CH-CH2-), 5.11-5.01 (m, 1H, -NH-), 4.30 (dd, J=11.9, 4.3Hz, 2H, -CH2-CH-CH2-), 4.15 (dd, J=11.9, 5.9Hz, 2H, -CH2-CH-CH2-), 3.82 (s, 6H, 2×-OCH3), 3.33-3.19 (m, 2H, -CH2-NH-), 2.37-2.24 (m, 6H, 3×-CH2-COO-), 2.09-1.91 (m, 8H, 2×-CH2-CH=CH-CH2-), 1.68-1.50 (m, 8H, -CH2-CH2-NH- and 3×-CH2-CH2-COO-), 1.38-1.21 (m, 50H, 25×-CH2-), 0.91-0.83 (m, 6H, 2×-CH3). 13C NMR (75MHz, CDCl3) delta 173.4, 172.9, 161.1, 154.6, 150.8, 139.4, 134.4, 130.1, 129.8, 128.7, 128.5, 127.5, 121.9, 104.7, 100.1, 69.0, 62.2, 55.5, 41.4, 34.3, 34.1, 32.0, 29.9, 29.8, 29.6, 29.4, 29.4, 29.3, 29.3, 29.2, 29.2, 29.1, 27.3, 27.3, 26.8, 25.0, 22.8, 14.2. ESI-MS (ESI+): 1073m/z [M+H]+, 1090m/z [M+NH4]+, 1095m/z [M+Na]+, 1111m/z [M+K]+. Purity ?95% (HPLC)

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 135,p. 77 - 88

49
[ 537-42-8 ]
C₁₆H₁₅Cl₂O₄P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		(1) In a dry 250 ml three-necked round bottom flask, E-4'-hydroxy-3,5-dimethoxydystyrene (<strong>[537-42-8]pterostilbene</strong>, 20 mmol, 5.12 g) was added, dissolved in 40 ml of CH2Cl2. Equip with spherical condenser and anhydrous calcium chloride drying tube, and thermometer. Using 10ml of CH2Cl2 to dissolve 5.6ml POCl3 (60mmol) and using a constant pressure dropping funnel slowly add dropwise. During the adding dropwise process, maintain at 10 deg.C. In 1h, dropping is finished. Continue stirring for 1 h. Using 10ml of CH2Cl2 to dissolve 5.6ml Et3N (40mmol) and place into the constant pressure dropping funnel. In 15min, the addition is finished. After adding is complete, continue stirring for 4h. The reaction is completed, remove the drying tube, add 40ml of distilled water, continue stirring for 30min. The reaction solution was poured into a separatory funnel and the CH2Cl2 layer was separated. The aqueous layer was extracted three times with CH2Cl2. All CH2Cl2 layers were combined, washed twice with water, dried and dried to give a yellow oily phosphorylated intermediate. Slowly add dropwise 1M NaOH (4 g/100 ml). The reaction temperature was controlled at 30 C. Add until pH = 6. A large amount of white precipitated out and place in a refrigerator overnight. And the mixture was washed with a small amount of water and washed with acetone to obtain 6.30 g of a white flake E-3,5-dimethoxystyryl-4'-O-phosphate monosodium salt in a yield of 88%. Purity 99%.

Reference： [1]Patent: CN106146548,2016,A .Location in patent: Paragraph 0062

50
[ 2628-16-2 ]
[ 20469-65-2 ]
[ 537-42-8 ]

Yield	Reaction Conditions	Operation in experiment
52%Chromat.	With potassium carbonate; In ethanol; water; at 150℃; for 0.5h;Microwave irradiation; Sealed tube; Green chemistry;	General procedure: The experimental procedure for MW-assisted Mizoroki-Heckcoupling reactions was carried out analogously to the procedure previously reported [47]. Into a 10 mL MW tube equippedwith a magnetic stirring bar, aryl halide 1a-h (0.25 mmol),K2CO3 (0.5 mmol), olefin 2a-d (0.3 mmol), ethanol (0.5 mL)and water (to obtain a total volume of 2 mL taking into accountthe volume of Pd NPs solution) were added. Finally, the required volume of the Pd NPs dispersion was added. Then, thereaction tube was sealed with a rubber cap and heated at130-150 C for 5-30 minutes under MW irradiation (fixed temperature method) using air cooling. After that, the reaction mixture was cooled to room temperature, extracted three times withethyl acetate (15 mL each) and dried with anhydrous Na2SO4.The stilbene products 3-15 were purified by silica gel columnchromatography. The products were characterized by 1H NMR,13C NMR, and GC-MS. All spectroscopic data were in agreement with those previously reported for the following compounds: (E)-1-(4-styrylphenyl)ethanone (3) [64], (E)-phenyl(4-styrylphenyl)methanone (4) [64], (E)-3-styrylquinoline (5) [55],(E)-1,3-dimethoxy-5-styrylbenzene (6) [64], (E)-1-methoxy-4-styrylbenzene (7) [64], (E)-1-methyl-4-styrylbenzene (8) [65],(E)-1-methyl-2-styrylbenzene (9) [65], (E)-4-styrylphenol (10)[66], (E)-4-(3,5-dimethoxystyryl)pyridine (14) [67], 1-(4-(2,2-diphenylvinyl)phenyl)ethanone (15) [56], and (E)-4-(3,5-dimethoxystyryl)phenol or pterostilbene (19) [60].

Reference： [1]Beilstein Journal of Organic Chemistry,2017,vol. 13,p. 1717 - 1727

51
[ 537-42-8 ]
2,4-dichloro-6-{4-[4-(1,2,2-triphenylethenyl)phenyl]-1H-1,2,3-triazol-1-yl}-1,3,5-triazine [ No CAS ]
2-chloro-4-{4-[2-(3,5-dimethoxy-phenyl)-vinyl]-phenoxy}-6-[5-(4-triphenylvinyl-phenyl)-[1,2,3]triazol-1-yl]-[1,3,5]triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In methanol; at 60℃; for 10h;	In a 50 ml reaction vessel, 12.00 g of sandalwood stilbene, 9.0 g of sodium hydroxide, 0.12 g of fluorescent label III and20mL methanol, the temperature control at 60 under the conditions of reaction 10h. After the completion of the reaction, after the completion of the reaction, the reaction solvent was dried, and the reaction was carried out To get the product.

Reference： [1]Patent: CN106967049,2017,A .Location in patent: Paragraph 0027; 0028; 0029; 0030; 0031; 0032; 0033

52
[ 537-42-8 ]
[ 42017-89-0 ]
[ 1094101-40-2 ]

Yield	Reaction Conditions	Operation in experiment
65%		To a mixed solution of methylene chloride / N, N-dimethylacetamide 20/1 (63 ml) at room temperature was added SOCl 2 (2.76 g, 0.02 mol) 2-methylpropanoic acid (3.18 g, 0.01 mol) was added to the mixture, and the mixture was stirred at room temperature for 2 hours. " (E) -4- (3,5-dimethoxystyryl) phenol (5.12 g, 0.02 mol) was added and the reaction was warmed to 60-65 & lt; The mixture was stirred overnight on the road. The reaction mixture was cooled to 0 & lt; 0 & gt; C and slowly added 100 ml of purified water. Get The crude mixture was stirred at room temperature for 0.5 h. Extract with 100 ml of ethyl acetate and wash 3 times with 150 ml of brine Followed by distillation under reduced pressure. Purification by column chromatography (30% ethyl acetate in hexanes) gave 65% yield as a white Obtained a color solid.

Reference： [1]Patent: KR2017/55610,2017,A .Location in patent: Paragraph 0088-0091

53
[ 537-42-8 ]
[ 20260-53-1 ]
C₂₂H₁₉NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine; In acetone; for 12h;Inert atmosphere; Reflux;	Pterostilbene (2.00 g, 7.8 mmol, 1.0 eq) was solubilizedin acetone (10 mL), followed by the addition ofnicotinoyl chloride hydrogen chloride (1.67 g, 9.36 mmol,1.2 eq) and TEA (3.26 mL, 23.41 mmol, 3.0 eq) and thenheated to reflux, under an atmosphere of N2 for 12 h. Themixture was then filtered, and concentrated under reducedpressure. The solid was concentrated and purified using biotage silica column chromatography using an eluent of50% EtOAc in pet ether, to yield the desired product as awhite fluffy solid in 85% yield.[0686] Eta NMR (CDC13, 400 MHz): delta ppm 9.41 (1Eta, s),8.87 (1Eta, dd, J=4.8, 3.2 Hz), 8.46 (1Eta, d, J=8.0 Hz), 7.58(2Eta, d, J=8.3 Hz), 7.48 (1Eta, dd, J=7.8, 5.0 Hz), 7.24 (2Eta,m), 7.02 (2Eta, m), 6.68 (2Eta, m), 6.42 (1Eta, s), 3.84 (6Eta, s).13C NMR (CDC13, 125 MHz): delta ppm 163.9, 161.0, 154.0,151.4, 149.9, 139.1, 137.6, 135.4, 129.2, 127.6, 125.6,125.3, 121.8, 104.7, 100.1, 55.4. HRMS (ES, M+H+) calculated362.1398 for C22H20NO4, found 362.1392.

Reference： [1]Patent: US2017/267709,2017,A1 .Location in patent: Paragraph 0684-0686

54
[ 537-42-8 ]
[ 74808-10-9 ]
(E)-1-(3-methoxy-4'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl)-2-(5-methoxyphenyl) ethene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With boron trifluoride diethyl etherate; In dichloromethane; for 0.5h;Inert atmosphere;	General procedure: 2,3,4,6-tetra-O-acetyl-alpha/beta-d-glucopyranosyl trichloroacetimidate 46 [72] or per-O-acetyl-alpha/beta-d-maltopyranosyl trichloroacetimidate 47 [73] (1mmol) was dissolved in anhydrous CH2Cl2 (10mL) in a 50mL round-bottomed flask under argon atmosphere. Methylated resveratrol derivative (0.33mmol) and boron trifluoride diethyl etherate (0.033mmol) were added to the stirring solution. After 30min the reaction was stopped with triethylamine (5mL) and concentrated. The crude product was purified by flash column chromatography using different hexane/ethyl acetate mixtures with 1% TEA.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 146,p. 123 - 138

55
[ 537-42-8 ]
[ 250330-63-3 ]
C₅₄H₆₆O₂₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With boron trifluoride diethyl etherate; In dichloromethane; for 0.5h;Inert atmosphere;	General procedure: 2,3,4,6-tetra-O-acetyl-alpha/beta-d-glucopyranosyl trichloroacetimidate 46 [72] or per-O-acetyl-alpha/beta-d-maltopyranosyl trichloroacetimidate 47 [73] (1mmol) was dissolved in anhydrous CH2Cl2 (10mL) in a 50mL round-bottomed flask under argon atmosphere. Methylated resveratrol derivative (0.33mmol) and boron trifluoride diethyl etherate (0.033mmol) were added to the stirring solution. After 30min the reaction was stopped with triethylamine (5mL) and concentrated. The crude product was purified by flash column chromatography using different hexane/ethyl acetate mixtures with 1% TEA.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 146,p. 123 - 138

56
[ 537-42-8 ]
(E)-4-(3,5-dimethoxystyryl)phenoxysulfonyl fluoride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		Triethylamine (220 muL, 1.59 mmol) was added to the rosewood at room temperature.[Compound 48] (272 mg, 1.04 mmol) in acetonitrile (1 mL)After stirring for 10 minutes,A solution of 1-(fluorosulfonyl)-2-3-dimethyl-1H-imidazole trifluoromethanesulfonate [Compound 4] (448 mg, 1.27 mmol) in acetonitrile (1 mL) was added to the system in one portion and under argon Under protection 1h,TLC (petroleum ether:Ethyl acetate=4:1, product Rf=0.43)Column chromatography (silica gel 300-400 mesh, petroleum ether:Ethyl acetate = 4:1, 3:1) to give a pale yellow solid(E)-4-(3,5-dimethoxystyryl)phenoxysulfonyl fluoride[Compound 49] (309 mg, 87%) (scheme 22).

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 2605 - 2610
Angew. Chem.,2018,vol. 130,p. 2635 - 2640,6
[2]Patent: CN107857730,2018,A .Location in patent: Paragraph 0204; 0205; 0206; 0207; 0208; 0209

57
[ 67843-74-7 ]
[ 537-42-8 ]
(S,E)-2-((4-(3,5-dimethoxystyryl)phenoxy)methyl)oxirane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68.1%	With potassium carbonate; In acetonitrile; for 12h;Reflux; Inert atmosphere; Darkness;	General procedure: A mixture of <strong>[537-42-8]pterostilbene</strong> (1.0 g, 3.902 mmol), epichlorohydrin(0.61 mL, 7.804 mmol) and anhydrous potassium carbonate (1.22g, 8.854 mmol) in 30 mL acetonitrile was refluxed in flask for 12h under dark in a nitrogen atmosphere, then the solvent wasremoved under reduced pressure. The residue was added water(50 mL), and extracted with dichloromethane (20 mL 3). Thecombined organic layers were washed with brine (30 mL 3),dried over anhydrous sodium sulfate, and filtered. The resultingproduct was further purified using preparative thin layerchromatography.

Reference： [1]Bioorganic Chemistry,2018,vol. 78,p. 298 - 306

58
[ 51594-55-9 ]
[ 537-42-8 ]
(R,E)-2-((4-(3,5-dimethoxystyryl)phenoxy)methyl)oxirane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82.1%	With potassium carbonate; In acetonitrile; for 12h;Reflux; Inert atmosphere; Darkness;	General procedure: A mixture of <strong>[537-42-8]pterostilbene</strong> (1.0 g, 3.902 mmol), epichlorohydrin(0.61 mL, 7.804 mmol) and anhydrous potassium carbonate (1.22g, 8.854 mmol) in 30 mL acetonitrile was refluxed in flask for 12h under dark in a nitrogen atmosphere, then the solvent wasremoved under reduced pressure. The residue was added water(50 mL), and extracted with dichloromethane (20 mL 3). Thecombined organic layers were washed with brine (30 mL 3),dried over anhydrous sodium sulfate, and filtered. The resultingproduct was further purified using preparative thin layerchromatography.

Reference： [1]Bioorganic Chemistry,2018,vol. 78,p. 298 - 306

59
[ 537-42-8 ]
(E)-4-((±)-3-(3,5-dimethoxyphenyl)-5-(3,5-dimethoxystyryl)-2,3-dihydrobenzofuran-2-yl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With silver(I) acetate; In methanol; at 50℃; for 1h;	After stirring of46 <strong>[537-42-8]pterostilbene</strong> (1b, 0.39 mmol) and AgOAc (0.54 mmol) in MeOH (5 mL) at 50C for 1 h,47 the resultant solution was concentrated in vacuo. The residue was purified using silica gel48 column chromatography eluted with CHCl3/MeOH (10/1) and HPLC (70% MeCN49 elution), to afford 2b.50 Pterostilbene trans-dehydrodimer (2b): 41% yield. IR (ATR): numax 3371, 2925, 1588,51 1201, 1147 cm-1; 1H NMR (400 MHz, Acetone-d6): delta 7.45 (1H, d, J = 9.2 and 1.4 Hz,52 H-6), 7.24-7.26 (3H, m, Ar), 7.20 (1H, d, J = 17.0 Hz, -CH=CH-), 6.97 (1H, d, J = 17.053 Hz, -CH=CH-), 6.89 (1H, d, J = 8.7 Hz, H-7), 6.86 (2H, d, J = 8.7 Hz, Ar), 6.73 (2H, d, J54 = 2.3 Hz, Ar), 6.42-6.45 (3H, m ,Ar), 6.36 (1H, d, J = 2.6 Hz, Ar), 5.57 (1H, d, J = 8.7 Hz,55 H-2), 4.58 (1H, d, J = 8.2 Hz, H-3), 3.78 (6H, s, 2OCH3), 3.74 (6H, s, 2OCH3); 13C NMR56 (100 MHz, Acetone-d6): delta 161.4, 161.2, 159.8, 157.7, 144.2, 140.0, 131.5, 131.4, 130.9,57 129.0, 127.9, 127.8, 126.1, 123.1, 115.4, 115.3, 109.5, 106.4, 104.2, 99.5, 98.7, 93.0, 57.3,58 54.7HRESITOFMS: m/z 511.2128 [M+H]+ (calcd. for C32H31O6, 511.2121).

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 3741 - 3753
[2]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 2475 - 2479
[3]Molecules,2019,vol. 24

60
[ 537-42-8 ]
[ 100-11-8 ]
1,3-dimethoxy-5-(4-((4-nitrobenzyl)oxy)styryl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	The title compound (STL) is synthesized as follows; About 0.5 gof <strong>[537-42-8]pterostilbene</strong>, 0.42 g of 1-(bromomethyl)-4-nitrobenzene and 3equivalence of potassium carbonate (0.786 g) in the DMF solventwas kept for reaction overnight under stirring at room temperature.The reaction is monitored by using TLC with the 3:2 ratios of petroleumether and chloroform as a solvent system. The reactionmixture was extracted by ethyl acetate. The unreacted startingmaterial is removed by 10% sodium hydroxide, the crude product ispurified by column chromatography using 3:2 ratios of Petroleumether and chloroform resulting the product, 1,3-dimethoxy-5-(4-((4-nitrobenzyl)oxy)styryl)benzene (STL). The fine yellow crystalsof product were grown using DMF as solvent. Yield: 82%; yellow crystal; MP: 154-155C; For LC-MS, 1HNMRand 13C NMR [See Supplementary file].

Reference： [1]Journal of Molecular Structure,2018,vol. 1173,p. 300 - 306

61
[ 20469-65-2 ]
[ 2628-17-3 ]
[ 537-42-8 ]

Yield	Reaction Conditions	Operation in experiment
56.23%	With tetrabutylammomium bromide; palladium diacetate; potassium carbonate; triphenylphosphine; In water; N,N-dimethyl-formamide; at 120℃; for 8h;	Add 4-hydroxystyrene (0.5 g, 4.16 mmol) to a 50 ml round bottom flask.Dissolve it by adding 15 mL of DMF.Then 3,5-dimethoxybromobenzene (1.3 g, 5.99 mmol) was added in sequence.An aqueous solution of potassium carbonate (1.3 g, dissolved in 10 mL of water),Tetrabutylammonium bromide (134.2 mg, 0.42 mmol),Palladium acetate (46.7 mg, 0.21 mmol),Triphenylphosphine (131.0 mg, 0.50 mmol),Heated to 120 C reaction, 8 hours after TLC detection,The reaction is over.Cool to room temperature,Diatomaceous earth suction filtration,The filtrate was extracted with ethyl acetate (50 mL×3).Combine the organic phase,The organic phase was washed with saturated brine (200 mL×6).Dry over anhydrous sodium sulfate,filter,The filtrate was evaporated to dryness under reduced pressure at 50 C to yield 1.6 g of red-black oil.Column chromatography (ethyl acetate: petroleum ether = 1:20, 2.5L) affordedThe yield was 56.23%.

Reference： [1]Patent: CN108484374,2018,A .Location in patent: Paragraph 0033; 0034; 0039; 0044
[2]Bioorganic Chemistry,2020,vol. 100

62
[ 358-23-6 ]
[ 537-42-8 ]
[ 2271159-94-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With pyridine In dichloromethane at 0℃; for 2h; Inert atmosphere;
87%	With pyridine In dichloromethane at 0 - 20℃; for 0.583333h; Inert atmosphere;	Step 1 To a 250 mL flask equipped with a stir bar, pterosilben (20 mmol, 1.0 equiv, 5.12 g), and pyridine (22 mmol, 1.1 equiv, 3.77 mL) were mixed with DCM (80 mL)under argon atmosphere. The reaction mixture was stirred at 0oC, and Tf2O (22 mmol, 1.1 equiv, 3.70 mL) was dropwise added into reaction system over 5 min. The reaction mixture was then allowed to warm to room temperature and stirred for 30 min. Upon completion, water (100 mL) was added to quench the reaction. The reaction mixture was then extracted with DCM (30 mL x 3). The combined organic extracts were dried with anhydrous Na2SO4and concentrated under vacuum. The crude product was purified by flash column chromatography on silica gel to afford the corresponding trifluoromethanesulfonic ester (6.78 g, 87% yield).

Reference： [1]Wu, Jiang; Zhao, Qunchao; Wilson, Thomas C.; Verhoog, Stefan; Lu, Long; Gouverneur, Véronique; Shen, Qilong [Angewandte Chemie - International Edition, 2019, vol. 58, # 8, p. 2413 - 2417][Angew. Chem., 2019, vol. 131, # 8, p. 2435 - 2439,5]
[2]Liang, Junqing; Dong, Lefeng; Qian, Feng; Kong, Yijin; Wang, Mingxia; Xu, Xiaoyong; Shao, Xusheng; Li, Zhong [Chinese Chemical Letters, 2022, vol. 33, # 11, p. 4817 - 4821]

63
[ 74-83-9 ]
[ 537-42-8 ]
[ 22255-22-7 ]

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 175,p. 114 - 128
[2]Patent: CN110041204,2019,A .Location in patent: Paragraph 0024; 0027

64
C₂₃H₂₂O₄ [ No CAS ]
[ 537-42-8 ]

Yield	Reaction Conditions	Operation in experiment
44.6 g	With hydrogen; at 25 - 120℃; under 6000.6 Torr; for 4h;	55.6 g of 3,5-dimethoxybenzyl iodide, 42.4 g of 4-benzyloxybenzaldehyde, 3 g of a 5 wt% palladium carbon catalyst and 400 g of toluene were mixed, and heated to 100 C for 5 hours, and the resulting reaction was carried out. The solution is cooled to below 25 C; the gas in the reaction vessel is replaced with hydrogen, and then hydrogen is introduced to a pressure of 8 kg·f/cm 2 , and then the temperature is raised to 120 C, and the reaction is continued for 4 hours;The obtained reaction liquid was filtered to recover a catalyst, and the mother liquid was evaporated to dryness, and the solid obtained by evaporation to dryness was heated to 85 C with 50 g of toluene, and then cooled to 10 C, filtered and dried.44.6 g of rosewood was obtained, and the yield was 87.1%.The purity was 99.5% by liquid chromatography.

Reference： [1]Patent: CN109970517,2019,A .Location in patent: Paragraph 0058; 0059; 0076; 0077; 0079; 0080

65
C₂₃H₂₂O₄ [ No CAS ]
[ 537-42-8 ]

Yield	Reaction Conditions	Operation in experiment
45.5 g	With hydrogen; at 25 - 120℃; under 6000.6 Torr; for 4h;	reparation of red sandalwood will be 46.5 grams4-benzyloxybenzyl chloride, 33.2 g3,5-dimethoxybenzaldehyde, 2 g of a 5 wt% palladium carbon catalyst and 400 g of toluene are mixed, and after heating to 100 C for 5 hours, the resulting reaction solution is cooled to 25 C or less;The gas in the reaction vessel was replaced with hydrogen gas, and then hydrogen gas was introduced to a pressure of 8 kg·f/cm 2 , and then the temperature was raised to 120 C, and the reaction was continued for 4 hours;The obtained reaction liquid is filtered to recover the catalyst, and the mother liquid is evaporated to dryness.The solid obtained by evaporation to dryness was heated to 85 C with 50 g of toluene, then cooled to 10 C and dried by filtration.Got 45.5 grams of rosewood,The yield is 88.9%.The purity was 99.6% by liquid chromatography.

Reference： [1]Patent: CN109970517,2019,A .Location in patent: Paragraph 0082-0084

66
[ 106-41-2 ]
[ 1073354-86-5 ]
[ 537-42-8 ]

Yield	Reaction Conditions	Operation in experiment
43%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In ethanol; at 110℃; for 0.5h;Microwave irradiation; Sealed tube;	General procedure: To a solution of trans-2-(3,5-dimethoxyphenyl)-vinylboronic acid pinacol ester (1.2 mmol) in EtOH abs. (2,5 mL), [1,1? bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.005 mmol), K2CO3 anhydrous (2 mmol) and the corresponding brominated compound (1 mmol) were added. The reaction mixture was stirred and irradiated by microwave at 110 C for 30 min. Then the reaction was filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel using hexane/ ethyl acetate (from 95:5 to 7:3) as eluent to give the corresponding derivatives. 4.1.2 4-(3,5-dimethoxystyryl)phenol (3) Yield: 43%. Rf: 0.4 in 8:2 hexane/ ethyl acetate 1H NMR (CDCl3, 300 MHz): delta: 7.42 (d, 2H); 6.99 (dd, 2H); 6.85 (d, 2H); 6.68 (s, 2H); 6.42 (t, 1H); 3.86 (s, 6H). 13C NMR (CDCl3, 300 MHz): delta 55.4, 99.7, 104.4, 115.7, 126.6, 128.0, 128.7, 130.1, 139.7, 155.4, 160.9 ESI(m/z): 256.3 [M+ + 1].

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 180,p. 637 - 647

67
[ 537-42-8 ]
[ 10083-24-6 ]

Reference： [1]Molecules,2019,vol. 24

68
[ 537-42-8 ]
[ 49558-03-4 ]
[ 2304727-68-0 ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 3,5-dimethoxy-4'-hydroxy-trans-stilbene With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,2-dichloro-ethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: 4-nitro-3-phenylfuroxan In 1,2-dichloro-ethane at 55℃; Inert atmosphere;	5.3. General procedures for the synthesis of compounds 10d-f General procedure: Compounds 12a-b and 13 were synthesized according to previously described methodologies [16]. A mixture containing 4-(3,5-dimethoxystyryl)phenol (13) (0.97mmol), DBU (1.33mmol), and 7mL of dry 1,2-dichloroethane was stirred under a nitrogen atmosphere at the room temperature for 15min. Afterward, the N-oxide derivative (4 or 5 or 6) (1mmol) was added in the medium. The reaction was kept under stirring conditions at 55°C for 2-8h and monitored by TLC. The product was isolated by diluting the reaction medium with approximately 60mL of 1,2-dichloroethane. The organic phase was washed with distilled water (4×15mL) and dried with sodium sulfate or magnesium sulfate. After filtration, the organic phase was concentrated under a reduced pressure to produce the crude, which was purified by column chromatography (flash silica; eluent: dichloromethane: petroleum ether, 7:3 (v/v)) providing compounds 10d-f at yields ranging from 30 to 60% as described.

Reference： [1]Andersen, Olaf Sparre; Barbieri, Karina Pereira; Bosquesi, Priscila Longhin; Carlos, Iracilda Zepone; Chelucci, Rafael Consolin; Costa, Fernando Ferreira; Dos Santos, Jean Leandro; Fernandes, Guilherme Felipe dos Santos; Lanaro, Carolina; Melchior, Aylime Castanho Bolognesi; Pavan, Aline Renata; Rusinova, Radda; de Souza, Cristiane Maria [Bioorganic Chemistry, 2020, vol. 100]

69
[ 537-42-8 ]
[ 943-89-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
69%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 60℃; for 24h;	4.2. General Procedure for the Synthesis of Compound 2a-i General procedure: Pterostilbene (0.42 g, 1.65 mmol), selected cinnamic acid (1.5 mmol), N-Ethyl-N0-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI, 0.32 g, 1.65 mmol), and4-dimethylaminopyridine (DMAP, 0.02 g, 0.15 mmol) were added together and dissolvedin 20 mL acetonitrile. The mixture was refluxed at 60 C for 24-48 h. After the reactionwas completed (monitored by TLC), the mixture was concentrated in a vacuum. Then, thecrude product was purified with silica gel column chromatography, using dichloromethaneas the mobile phase. The target product was obtained in a 7-80% yield.