Name: 480-44-4|5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one|98%
Brand: Ambeed
SKU: A123393
Price: 5.0 USD
Availability: InStock
Rating: 94 (22 reviews)

1
[ 186581-53-3 ]
[ 480-44-4 ]
[ 5128-44-9 ]

Reference： [1]Archiv der Pharmazie,1936,vol. 274,p. 126,136, 143

2
[ 480-44-4 ]
[ 77-78-1 ]
[ 5128-44-9 ]

Reference： [1]Proceedings - Indian Academy of Sciences, Section A,1949,p. 72,75
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1956,vol. 76,p. 453,454
Chem.Abstr.,1956,p. 16759

3
[ 480-44-4 ]
5,7-dihydroxy-2-(4-methoxyphenyl)chroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetralin; palladium at 210℃;

Reference： [1]Massicot et al. [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1954, vol. 238, p. 111]

4
[ 480-44-4 ]
[ 4154-21-6 ]
[ 480-36-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; acetone Erhitzen des Reaktionsprodukts mit Acetanhydrid und Pyridin und Erwaermen des isolierten Reaktionsprodukts mit wss.-aethanol. Natronlauge;

Reference： [1]Zemplen; Bognar [Chemische Berichte, 1941, vol. 74, p. 1818,1821]

5
acacetin 7-O-β-D-galactopyranoside [ No CAS ]
[ 10257-28-0 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
18%	With hydrogenchloride In ethanol for 2h; on steam bath;

Reference： [1]Chatterjee, A.; Sarkar, S.; Saha, S. K. [Phytochemistry, 1981, vol. 20, # 7, p. 1760 - 1761]

6
[ 520-36-5 ]
[ 480-44-4 ]
[ 5128-44-9 ]

Reference： [1]Phytochemistry,1980,vol. 19,p. 741 - 746

7
[ 34339-69-0 ]
[ 480-44-4 ]
3''-O-benzyl-6-C-β-D-glucopyranosylacacetin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium methanolate In methanol; diethyl ether

Reference： [1]Bouillant; Besset; Favre-Bonvin; Chopin [Phytochemistry, 1980, vol. 19, # 8, p. 1755 - 1759]

8
[ 480-44-4 ]
[ 108-24-7 ]
[ 5892-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	at 140℃; for 1h;
	In pyridine
	With pyridine

Reference： [1]Bohlmann, Ferdinand; Banerjee, Shanta; Jakupovic, Jasmin; Grenz, Michael; Misra, Laxmi N.; et al. [Phytochemistry, 1985, vol. 24, # 3, p. 511 - 516]
[2]Thusoo; Raina; Ahmed [Journal of the Indian Chemical Society, 1982, vol. 59, # 8, p. 1007 - 1008]
[3]Hanamura, Shun; Hanaya, Kengo; Shoji, Mitsuru; Sugai, Takeshi [Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 128, p. 19 - 26]

9
[ 480-44-4 ]
[ 50730-31-9 ]
acacetin 7-O-L-arabinofuranoside [ No CAS ]
6-C-α-L-arabinofuranosylacacetin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium In methanol; chloroform for 0.5h; Ambient temperature;

Reference： [1]Besson, Elisabeth; Chopin, Jean [Phytochemistry, 1983, vol. 22, # 9, p. 2051 - 2056]

10
[ 480-44-4 ]
α-bromo-hexa-O-acetylrungiose [ No CAS ]
3''-O-α-L-rhamnopyranosyl-6-C-β-D-glucopyranosylacacetin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium methanolate In methanol; diethyl ether

Reference： [1]Bouillant; Besset; Favre-Bonvin; Chopin [Phytochemistry, 1980, vol. 19, # 8, p. 1755 - 1759]

11
[ 99474-26-7 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; acetic acid 1.) reflux, 4 h, 2.) 5 min; Yield given;
	With sulfuric acid In acetic acid at 95 - 100℃; Yield given;
	With sulfuric acid; acetic acid at 100℃; for 1h; Yield given;

Reference： [1]Saxena, Shabnam; Makrandi, J. K.; Grover, S. K. [Synthesis, 1985, # 6/7, p. 697]
[2]Cushman, Mark; Nagarathnam, Dhanapalan [Tetrahedron Letters, 1990, vol. 31, # 45, p. 6497 - 6500]
[3]Costantino; Rastelli; Albasini [European Journal of Medicinal Chemistry, 1996, vol. 31, # 9, p. 693 - 699]

12
[ 110865-07-1 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium methylate In ethanol; dichloromethane

Reference： [1]Le Floc'H, Yves; Lefeuvre, Martine [Tetrahedron Letters, 1986, vol. 27, # 45, p. 5503 - 5504]

13
[ 80443-16-9 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate In acetic acid for 3h; Heating;

Reference： [1]Chatterjee, A.; Sarkar, S.; Saha, S. K. [Phytochemistry, 1981, vol. 20, # 7, p. 1760 - 1761]

14
isosakuranetin 7-O-rhamnoside [ No CAS ]
[ 28161-50-4 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride at 100℃; for 3h;

Reference： [1]Doganca, S.; Ulubelen, A.; Tuzlaci, E. [Phytochemistry, 1989, vol. 28, # 12, p. 3561 - 3562]

15
[ 480-44-4 ]
[ 4154-21-6 ]
6''-O-α-L-rhamnopyranosyl-6-C-β-D-glucopyranosylacacetin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.7%	With lithium methanolate In methanol

Reference： [1]Bouillant; Besset; Favre-Bonvin; Chopin [Phytochemistry, 1980, vol. 19, # 8, p. 1755 - 1759]

16
[ 480-44-4 ]
[ 14227-66-8 ]
4''-O-β-D-glucopyranosyl-6-C-β-D-glucopyranosylacacetin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.7%	With lithium methanolate In methanol

Reference： [1]Bouillant; Besset; Favre-Bonvin; Chopin [Phytochemistry, 1980, vol. 19, # 8, p. 1755 - 1759]

17
[ 480-44-4 ]
[ 14227-90-8 ]
acacetin 7-O-L-arabinopyranoside [ No CAS ]
6,8-di-C-α-L-arabinopyranosylacacetin [ No CAS ]
6-C-α-L-arabinopyranosylacacetin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium In methanol; diethyl ether for 0.5h; Ambient temperature;

Reference： [1]Besson, Elisabeth; Chopin, Jean [Phytochemistry, 1983, vol. 22, # 9, p. 2051 - 2056]

18
[ 480-44-4 ]
[ 4163-60-4 ]
[ 80443-10-3 ]

Yield	Reaction Conditions	Operation in experiment
65 mg	With diethyl ether; boron trifluoride In dichloromethane for 24h;

Reference： [1]Chatterjee, A.; Sarkar, S.; Saha, S. K. [Phytochemistry, 1981, vol. 20, # 7, p. 1760 - 1761]

19
1-<2-hydroxy-4,6-bis(methoxymethoxy)phenyl>-3-(4-methoxyphenyl)propane-1,3-dione [ No CAS ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With Amberlyst 15 resin In isopropyl alcohol for 4h; Heating;

Reference： [1]Patonay, Tamas; Molnar, Denes; Muranyi, Zoltan [Bulletin de la Societe Chimique de France, 1995, vol. 132, # 2, p. 233 - 242]

20
acacetin-7-O-<β-D-glucopyranosyl(1->4)-α-D-xylopyranoside> [ No CAS ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid at 100℃; for 2h;

Reference： [1]Yadava, R. N.; Barsainya, Deepak [Journal of the Indian Chemical Society, 1997, vol. 74, # 10, p. 822 - 823]

21
[ 480-44-4 ]
6,8-diodoacacetin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N,N,N-trimethylbenzenemethanaminium dichloroiodate; calcium carbonate In methanol; dichloromethane at 20℃;

Reference： [1]Quintin, Jérôme; Lewin, Guy [Tetrahedron Letters, 2004, vol. 45, # 18, p. 3635 - 3638]

22
[ 5631-70-9 ]
[ 520-36-5 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 54% 2: 16%	With N-butyl-N-methylimidazolium heptachlorodialuminate In dichloromethane at 40℃; for 4h;

Reference： [1]Liu, Tao; Hu, Yongzhou [Synthetic Communications, 2004, vol. 34, # 17, p. 3209 - 3218]

23
[ 480-44-4 ]
[ 74-88-4 ]
[ 22395-14-8 ]
[ 5631-70-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 41% 2: 47%	With potassium carbonate

Reference： [1]Wang, Cai-Ling; Zheng, Xing; Meng, Wei-Dong; Li, Hong-Qi; Qing, Feng-Ling [Tetrahedron Letters, 2005, vol. 46, # 32, p. 5399 - 5402]

24
[ 108-73-6 ]
[ 2881-83-6 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	for 0.0583333h; microwave irradiation;
71%	With dmap at 200℃; for 3h; Inert atmosphere;	4'-Methoxy-5,7-dihydroxyflavone (acacetin, 1a) A solution of phloroglucinol (1.0 g, 7.93 mmol), ethyl 4-methoxybenzoyl acetate (2.9 g, 13.0 mmol) and DMAP (0.073 g, 0.6 mmol) was stirred and refluxed at 200 oC under nitrogen protection for 3 h. The mixture was then cooled to room temperature and diluted with EtOAc (10 mL). The resulting precipitate was filtered and washed with EtOAc (10 mL) to obtain crude solid which was subsequently decolorized with activated carbon and recrystallized in THF to obtain pure compound 1a as a yellow solid (1.6 g, 5.63 mmol, 71%). 1H NMR (400 MHz, DMSO-d6): δ 12.92 (s, 1H), 10.85 (br s, 1H), 8.01 (d, J = 8.8 Hz, 2H), 7.09 (d, J = 8.8 Hz, 2H), 6.84 (s, 1H), 6.49 (d, J = 1.6 Hz, 1H), 6.20 (d, J = 2.0 Hz, 1H), 3.85 (s, 3H); 13C NMR (100 MHz, DMSO-d6): δ 182.2, 164.7, 163.7, 162.7, 161.9, 157.8, 128.7, 123.3, 115.0, 104.2, 104.0, 99.3, 94.5, 56.0; ESI-MS [M-H]- (m/z): 283.08; data consistent with the literature 1-2.
44%	With dmap at 20 - 200℃; for 0.333333h; Inert atmosphere;

Reference： [1]Seijas, Julio A.; Vazquez-Tato, M. Pilar; Carballido-Reboredo, Raquel [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2855 - 2858]
[2]Zhao, Yuan; Cai, Li; Sui, Qiang; Lin, Feng; Jiang, Wen; Chen, Jianli; Lu, Weigeng; Gao, Qi [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3577 - 3580]
[3]Letribot, Boris; Nascimento, Megane; Cerrato, Giulia; Darrigrand, Romain; Salgues, Valerie; Renko, Dolor; Pruvost, Alain; Alami, Mouad; Messaoudi, Samir; Apcher, Sebastien [Journal of Medicinal Chemistry, 2022, vol. 65, # 6, p. 4633 - 4648]

25
[ 480-44-4 ]
[ 1939-99-7 ]
7-benzylsulfonylacacetin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine In tetrahydrofuran at 20℃; for 0.5h;

Reference： [1]Quintin, Jérôme; Roullier, Catherine; Thoret, Sylviane; Lewin, Guy [Tetrahedron, 2006, vol. 62, # 17, p. 4038 - 4051]

26
[ 480-44-4 ]
[ 108-24-7 ]
[ 101737-23-9 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; zinc(II) chloride at 140 - 150℃; for 2h;

Reference： [1]Gao, Hong; Kawabata, Jun [Bioscience, Biotechnology and Biochemistry, 2004, vol. 68, # 9, p. 1858 - 1864]

27
[ 480-66-0 ]
[ 100-07-2 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate In acetone at 65℃; for 24h; Inert atmosphere;	1.4. Synthesis of 2-p-methoxybenzyl-5,7-dihydroxychromone (2) To a solution of 2,4,6-trihydroxyacetophenone (1.68 g, 10 mmol) in acetone under argon/open atmosphere, was added K2CO3 (13.82 g, 100 mmol, 10 equiv). The mixture was stirred at room temperature for 10 min and then 4-methoxybenzoyl chloride (2.56 g, 15 mmol, 1.5 equiv) was added. The mixture was stirred under reflux for 24 h. After cooling to room temperature the undissolved K2CO3 was filtered off, washed with acetone and evaporated under reduced pressure to a residue. The crude mixture was extracted with ethyl acetate (30 mL × 3), washed with water, brine, dried with anhydrous Na2SO4 and concentrated under reduced pressure to a residue. The residue was purified by silica gel column chromatography using hexane/ethyl acetate (4:1) as eluent. Yield: 2.05 g (72%). Rf 0.17. Mp 138-142 °C. 1H NMR (400 MHz, DMSO) δ 2.07 (s, 1H), 2.63 (s, 1H), 3.56 (s, 3H), 6.29 (s, 1H), 6.96-7.11 (m, 2 H), 7.88-7.92 (m, 2H), 8.02-8.09 (m, 2H). 13C NMR (100.6 MHz, DMSO) δ 14.34, 30.79, 33.12, 40.13, 55.68, 60.51, 101.03, 108.68, 114.29, 130.25, 132.29, 156.56, 163.52, 204.59. MS (m/z): 285.27 (M + 1)+. Anal. Calcd for C16H12O5: C, 67.60; H, 4.25. Found: C, 67.49; H, 4.36.
71%	Stage #1: 2,4,6-trihydroxyacetophenone With potassium carbonate In acetone at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 4-methoxy-benzoyl chloride In acetone at 60℃; for 24h; Inert atmosphere;	2.1; 2.2; 2.3; 2.4; 2.5 Preparation of 5,7-dihydroxy-4'-methoxyflavone III Step 2-1, under nitrogen protection, weighed 59.5mmo (l10g) 2,4,6-trihydroxyacetophenone II, 594.7mmol (82.2g) of potassium carbonate and 100ml of acetone was added to a second three-necked flask, After stirring at room temperature for 10 minutes, 89.2 mmol (15.2 g) of p-methoxybenzoyl chloride was weighed into a second three-necked flask to obtain a mixture II.Step 2-2, the mixture was stirred at 60°C for 24 hours, cooled to room temperature to obtain the reaction solutionII.Step 2-3, the reaction solution II was filtered and washed with acetone to obtain a filtrate I. Step 2-4, the filtrate I was extracted three times with 200ml of ethyl acetate, washed with water, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and evaporated to remove ethyl acetate to obtain a solid powder I.Step 2-5, the solid powder I was subjected to column chromatography using a solution of hexane: ethyl acetate = 4: 1 in a volume ratio to obtain 12 g of a solid powder.
45%	Stage #1: 2,4,6-trihydroxyacetophenone With potassium carbonate In acetone at 20℃; for 0.166667h; Stage #2: 4-methoxy-benzoyl chloride In acetone for 24h; Heating;

	Stage #1: 2,4,6-trihydroxyacetophenone; 4-methoxy-benzoyl chloride With potassium carbonate In pyridine at 120℃; for 3h; Heating / reflux; Stage #2: With potassium hydroxide; water In methanol for 20h; Heating / reflux; Stage #3: With acetic acid In water	9 To a solution of 80 ml dry pyridine was added 9.62 g 2',4',6'-trihydroxyacetophenone and 30 g anhydrous K2CO3 and 31 g 4-methoxybenzoyl chloride successively, then extracted reaction solution with chloroform when it was refluxed 3 hours at 120° C. by oil bath, and washed the chloroform extraction by water (100 ml), the chloroform was dried by anhydrous K2CO3 and decoloured by active carbon, then concentrated it in vacuo. The residue was dissolved with 60 ml anhydrous ethanol, and have deposition in solution, filtered it, afforded 13.53 g intermediate.To a solution of 50 ml methanol was added 6.3 g above intermediate and 6% KOH solution, stirred and refluxed it 20 hours, then recovered most of methanol in vacuo, and extracted it with chloroform to remove some extraneous component, the deposit was obtained after the water phase was acidified pH 9 by 10% acetic acid, and filtered it, washed by water, dried it, 1.83 g acacetin was obtained at last.
	Stage #1: 2,4,6-trihydroxyacetophenone; 4-methoxy-benzoyl chloride With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene for 8h; Reflux; Stage #2: With sodium hydroxide In 1,4-dioxane; methanol

Reference： [1]Location in patent: experimental part Zacharia, James T.; Hayashi, Masahiko [Carbohydrate Research, 2012, vol. 348, p. 91 - 94]
[2]Current Patent Assignee: UNIVERSITY OF SHANGHAI FOR SCIENCE AND TECHNOLOGY - CN107033112, 2017, A Location in patent: Paragraph 0028; 0029; 0030; 0031; 0032; 0033
[3]Gao, Hong; Kawabata, Jun [Bioscience, Biotechnology and Biochemistry, 2004, vol. 68, # 9, p. 1858 - 1864]
[4]Current Patent Assignee: THE UNIVERSITY OF HONG KONG - US2008/214493, 2008, A1 Location in patent: Page/Page column 10-11
[5]Lerdsirisuk, Pradith; Maicheen, Chirattikan; Ungwitayatorn, Jiraporn [Bioorganic Chemistry, 2014, vol. 57, p. 142 - 147]

28
[ 771481-08-4 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With ammonium formate In methanol for 2.5h; Heating;

Reference： [1]Quintin, Jerome; Lewin, Guy [Journal of Natural Products, 2004, vol. 67, # 9, p. 1624 - 1627]

29
[ 480-44-4 ]
[ 74-88-4 ]
[ 5128-44-9 ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; at 20℃; for 2h;	To a 0.75 ml pyridine was added 30 mg acacetin and several drops methyl iodide, stirred it 2 hours at room temperature, the residue was chromatographed, and eluted with petrol ether: acetone=2:1, afforded A-02-11-13.

Reference： [1]Journal of Natural Products,2004,vol. 67,p. 1624 - 1627
[2]Chemical Communications,2018,vol. 54,p. 2611 - 2614
[3]Patent: US2008/214493,2008,A1 .Location in patent: Page/Page column 11

30
[ 480-36-4 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With hydrogenchloride at 50 - 55℃; for 1.5h;

Reference： [1]Quintin, Jerome; Lewin, Guy [Journal of Natural Products, 2004, vol. 67, # 9, p. 1624 - 1627]

31
[ 771480-96-7 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 53 percent / HCOONH₄ / Pd/C / methanol / 5 h / Heating 2: 70 percent / aq. HCl / 1.5 h / 50 - 55 °C

Reference： [1]Quintin, Jerome; Lewin, Guy [Journal of Natural Products, 2004, vol. 67, # 9, p. 1624 - 1627]

32
[ 480-44-4 ]
[ 50848-66-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 95 percent / K₂CO₃ / dimethylformamide / 20 °C 2: 73 percent / benzyltrimethylammonium dichloroiodate; CaCO₃ / CH₂Cl₂; methanol / 20 °C

Reference： [1]Quintin, Jerome; Lewin, Guy [Journal of Natural Products, 2004, vol. 67, # 9, p. 1624 - 1627]

33
[ 520-34-3 ]
[ 480-44-4 ]

Reference： [1]Journal of Natural Products,2004,vol. 67,p. 1624 - 1627

34
[ 520-27-4 ]
[ 480-44-4 ]

Reference： [1]Journal of Natural Products,2004,vol. 67,p. 1624 - 1627

35
[ 159355-57-4 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 67 percent / KHCO₃ / dimethylformamide / 1 h / 120 °C 2: 68 percent / HCOONH₄ / Pd/C / methanol / 2.5 h / Heating

Reference： [1]Quintin, Jerome; Lewin, Guy [Journal of Natural Products, 2004, vol. 67, # 9, p. 1624 - 1627]

36
[ 480-44-4 ]
[ 529-53-3 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,2004,vol. 68,p. 1858 - 1864

37
[ 480-44-4 ]
7-benzylsulfonyl-6-nitroacacetin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 94 percent / triethylamine / tetrahydrofuran / 0.5 h / 20 °C 2: 39 percent / TFA; HNO₃ / 2 h / 0 °C

Reference： [1]Quintin, Jérôme; Roullier, Catherine; Thoret, Sylviane; Lewin, Guy [Tetrahedron, 2006, vol. 62, # 17, p. 4038 - 4051]

38
[ 480-44-4 ]
7-benzylsulfonyl-8-nitroacacetin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 94 percent / triethylamine / tetrahydrofuran / 0.5 h / 20 °C 2: 29 percent / TFA; HNO₃ / 2 h / 0 °C

Reference： [1]Quintin, Jérôme; Roullier, Catherine; Thoret, Sylviane; Lewin, Guy [Tetrahedron, 2006, vol. 62, # 17, p. 4038 - 4051]

39
[ 480-66-0 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) lithium bis(trimethyl)silyl amide / 1.) THF, -78 deg C, 3 h, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h 2: H₂SO₄, glacial AcOH / 1 h / 100 °C
	Multi-step reaction with 3 steps 1: pyridine / 3 h / on steam bath 2: 700 mg / KOH, pyridine / 2 h / 60 °C 3: NaOAc / acetic acid / 3 h / Heating
	Multi-step reaction with 3 steps 1: saturated aq. potassium carbonate / benzene / 0.33 h / 60 °C 2: tetrabutylammonium hydrogen sulfate / benzene; H₂O / 3 h / 60 °C 3: 1.) 5percent aq. potassium carbonate, 2.) glacial acetic acid / 1.) reflux, 4 h, 2.) 5 min

Multi-step reaction with 2 steps 1: 1) lithium bis(trimethyl)silyl amide (LiHMDS) / 1) THF, a) -78 deg C, b) -10 deg C, 2) THF, a) -78 deg C, b) room temp. 2: H₂SO₄ / acetic acid / 95 - 100 °C

Reference： [1]Costantino; Rastelli; Albasini [European Journal of Medicinal Chemistry, 1996, vol. 31, # 9, p. 693 - 699]
[2]Chatterjee, A.; Sarkar, S.; Saha, S. K. [Phytochemistry, 1981, vol. 20, # 7, p. 1760 - 1761]
[3]Saxena, Shabnam; Makrandi, J. K.; Grover, S. K. [Synthesis, 1985, # 6/7, p. 697]
[4]Cushman, Mark; Nagarathnam, Dhanapalan [Tetrahedron Letters, 1990, vol. 31, # 45, p. 6497 - 6500]

40
[ 108-73-6 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BF₃ 2: pyridine / 3 h / on steam bath 3: 700 mg / KOH, pyridine / 2 h / 60 °C 4: NaOAc / acetic acid / 3 h / Heating

Reference： [1]Chatterjee, A.; Sarkar, S.; Saha, S. K. [Phytochemistry, 1981, vol. 20, # 7, p. 1760 - 1761]

41
[ 480-44-4 ]
acacetin 7-O-β-D-galactopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 65 mg / BF₃/Et₂O / CH₂Cl₂ / 24 h 2: 11 mg / KHCO₃ / methanol; H₂O / 20 h / Ambient temperature
	Multi-step reaction with 2 steps 1: boron trifluoride diethyl etherate / dichloromethane / 3.5 h / -20 - -5 °C / Molecular sieve; Inert atmosphere 2: ammonia / methanol / 24 h / 20 °C
	Multi-step reaction with 2 steps 1: zinc(II) chloride / acetonitrile / -20 - -5 °C / Inert atmosphere 2: ammonia / methanol / 24 h / 20 °C

Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; potassium carbonate / chloroform / 12 h / 45 °C / Inert atmosphere 2: water; ammonium hydroxide / methanol / 12 h / 20 °C

Reference： [1]Chatterjee, A.; Sarkar, S.; Saha, S. K. [Phytochemistry, 1981, vol. 20, # 7, p. 1760 - 1761]
[2]Zacharia, James T.; Hayashi, Masahiko [Carbohydrate Research, 2012, vol. 348, p. 91 - 94]
[3]Zacharia, James T.; Hayashi, Masahiko [Carbohydrate Research, 2012, vol. 348, p. 91 - 94]
[4]Liu, Jidan; Chen, Ling; Cai, Shuanglian; Wang, Qiuan [Carbohydrate Research, 2012, vol. 357, p. 41 - 46]

42
[ 59115-98-9 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 700 mg / KOH, pyridine / 2 h / 60 °C 2: NaOAc / acetic acid / 3 h / Heating

Reference： [1]Chatterjee, A.; Sarkar, S.; Saha, S. K. [Phytochemistry, 1981, vol. 20, # 7, p. 1760 - 1761]

43
[ 80443-10-3 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 11 mg / KHCO₃ / methanol; H₂O / 20 h / Ambient temperature 2: 18 percent / 6 N HCl / ethanol / 2 h / on steam bath

Reference： [1]Chatterjee, A.; Sarkar, S.; Saha, S. K. [Phytochemistry, 1981, vol. 20, # 7, p. 1760 - 1761]

44
4-Methoxy-benzoic acid 2-acetyl-3,5-dihydroxy-phenyl ester [ No CAS ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrabutylammonium hydrogen sulfate / benzene; H₂O / 3 h / 60 °C 2: 1.) 5percent aq. potassium carbonate, 2.) glacial acetic acid / 1.) reflux, 4 h, 2.) 5 min

Reference： [1]Saxena, Shabnam; Makrandi, J. K.; Grover, S. K. [Synthesis, 1985, # 6/7, p. 697]

45
[ 100-07-2 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: saturated aq. potassium carbonate / benzene / 0.33 h / 60 °C 2: tetrabutylammonium hydrogen sulfate / benzene; H₂O / 3 h / 60 °C 3: 1.) 5percent aq. potassium carbonate, 2.) glacial acetic acid / 1.) reflux, 4 h, 2.) 5 min
	Multi-step reaction with 2 steps 1: 1) lithium bis(trimethyl)silyl amide (LiHMDS) / 1) THF, a) -78 deg C, b) -10 deg C, 2) THF, a) -78 deg C, b) room temp. 2: H₂SO₄ / acetic acid / 95 - 100 °C

Reference： [1]Saxena, Shabnam; Makrandi, J. K.; Grover, S. K. [Synthesis, 1985, # 6/7, p. 697]
[2]Cushman, Mark; Nagarathnam, Dhanapalan [Tetrahedron Letters, 1990, vol. 31, # 45, p. 6497 - 6500]

46
[ 100-09-4 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: anisoyl chloride; pyridine; benzene 2: sodium anisate / Verseifen des Reaktionsprodukts mit alkoholisch-waessriger-Kalilauge
	Multi-step reaction with 2 steps 1: thionyl chloride / 2 h / 60 °C 2: potassium carbonate / acetone / 24 h / 65 °C / Inert atmosphere

Reference： [1]Robinson; Venkataraman [Journal of the Chemical Society, 1926, p. 2346]
[2]Zacharia, James T.; Hayashi, Masahiko [Carbohydrate Research, 2012, vol. 348, p. 91 - 94]

47
[ 480-44-4 ]
[ 108-24-7 ]
C₁₈H₁₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine at 20℃; for 2h;	9 To a 0.75 ml pyridine was added 30 mg acacetin and 0.50 ml acetic anhydride, stirred it 2 hours at room temperature, the residue was chromatographed, and eluted with petrol ether: acetone=2:1, afforded A-02-1-11.

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF HONG KONG - US2008/214493, 2008, A1 Location in patent: Page/Page column 11

48
[ 480-66-0 ]
[ 100-07-2 ]
[ 1052063-34-9 ]
[ 1052063-33-8 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In pyridine at 120℃; for 3h; Heating / reflux;	9 To a solution of 80 ml dry pyridine was added 9.62 g 2',4',6'-trihydroxyacetophenone and 30 g anhydrous K2CO3 and 31 g 4-methoxybenzoyl chloride successively, then extracted reaction solution with chloroform when it was refluxed 3 hours at 120° C. by oil bath, and washed the chloroform extraction by water (100 ml), the chloroform was dried by anhydrous K2CO3 and decoloured by active carbon, then concentrated it in vacuo. The residue was dissolved with 60 ml anhydrous ethanol, and have deposition in solution, filtered it, afforded 13.53 g intermediate. The residue have three spots assayed by TALC, then chromatographed, and eluted with petrol ether: acetone=2:1, afforded A-2 (203 mg), A-3 (50 mg) and acacetin (1.83 g).

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF HONG KONG - US2008/214493, 2008, A1 Location in patent: Page/Page column 11

49
[ 74-96-4 ]
[ 480-44-4 ]
[ 1052063-32-7 ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine at 20℃; for 24h;	9 To a 0.75 ml pyridine was added 30 mg acacetin and several drops bromethyl, stirred it 24 hours at room temperature, the residue was chromatographed, and eluted with petrol ether: acetone=2:1, afforded A-02-11-14.

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF HONG KONG - US2008/214493, 2008, A1 Location in patent: Page/Page column 11

50
[ 480-44-4 ]
[ 93-97-0 ]
[ 73197-00-9 ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine at 20℃; for 2h;	9 To a 0.75 ml pyridine was added 30 mg acacetin and 0.50 ml benzoic anhydride, stirred it 2 hours at room temperature, the residue was chromatographed, and eluted with petrol ether: acetone=2:1, afforded A-02-11-12.

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF HONG KONG - US2008/214493, 2008, A1 Location in patent: Page/Page column 11

51
[ 126641-47-2 ]
[ 480-44-4 ]
C₃₀H₃₀O₁₄ [ No CAS ]
[ 80443-10-3 ]

Yield	Reaction Conditions	Operation in experiment
	With zinc(II) chloride In acetonitrile at -20 - -5℃; Inert atmosphere; optical yield given as %de; stereoselective reaction;

Reference： [1]Location in patent: scheme or table Zacharia, James T.; Hayashi, Masahiko [Carbohydrate Research, 2012, vol. 348, p. 91 - 94]

52
[ 126641-47-2 ]
[ 480-44-4 ]
[ 80443-10-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With boron trifluoride diethyl etherate In dichloromethane at -20 - -5℃; for 3.5h; Molecular sieve; Inert atmosphere; stereoselective reaction;	1.6. Synthesis of glycoside 4 Boron trifluoride etherate complex (0.027 g, 0.19 mmol, 0.13 equiv) was added to a stirred solution of glycosyl donor 3 (0.5 g, 1.43 mmol, 1.0 equiv), 2-p-methoxybenzyl-5,7-dihydroxychromone 2 (0.41 g, 1.43 mmol), and 10 equiv (by weight) of molecular sieves 4 Å in dichloromethane (5 mL) under argon atmosphere. The mixture was stirred for 1.5 h at -20 °C and then for a further 2 h at -5 °C. The mixture was then quenched with a saturated solution of NaHCO3 (20 mL) and extracted with chloroform (30 mL × 3). The combined organic layer was washed with water, dried with anhydrous Na2SO4, and concentrated under reduced pressure to a residue. The residue was purified by silica gel column chromatography using hexane/ethyl acetate (5:1) as eluent. Yield: 0.69 g (78%). Rf 0.38. Mp 118-122 °C. 1H NMR (400 MHz, DMSO) δ 1.9-2.1 (m, 12H), 2.50 (s, 1H), 3.35 (s, 3H), 3.89 (dd, 2H, J = 2.8, 6.4 Hz), 4.01 (m, 1H), 4.41 (dd, 1H, J = 6.4, 6.4 Hz), 5.08 (dd, 1H, J = 2.0, 8.4 Hz), 5.33 (dd, 1H, J = 4.0, 6.8 Hz), 5.89 (d, 1H, J = 8.4 Hz), 6.31 (s, 1H), 7.14 (m, 2H), 8.10 (m, 4H). 13C NMR (100.6 MHz, DMSO) δ 20.31, 39.71, 55.68, 61.23, 67.62, 69.93, 70.82, 91.27, 100.88, 114.34, 132.16, 162.89, 169.92. MS (m/z): 614.99 (M+1)+. Anal. Calcd for C30H30O14: C, 58.63; H, 4.92. Found: C, 58.41; H, 5.06.

Reference： [1]Location in patent: experimental part Zacharia, James T.; Hayashi, Masahiko [Carbohydrate Research, 2012, vol. 348, p. 91 - 94]

53
2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl fluoride [ No CAS ]
[ 480-44-4 ]
C₃₀H₃₀O₁₄ [ No CAS ]
[ 80443-10-3 ]

Yield	Reaction Conditions	Operation in experiment
	With boron trifluoride diethyl etherate In dichloromethane at -20 - -5℃; Inert atmosphere; stereoselective reaction;	1.6. Synthesis of glycoside 4 Boron trifluoride etherate complex (0.027 g, 0.19 mmol, 0.13 equiv) was added to a stirred solution of glycosyl donor 3 (0.5 g, 1.43 mmol, 1.0 equiv), 2-p-methoxybenzyl-5,7-dihydroxychromone 2 (0.41 g, 1.43 mmol), and 10 equiv (by weight) of molecular sieves 4 Å in dichloromethane (5 mL) under argon atmosphere. The mixture was stirred for 1.5 h at -20 °C and then for a further 2 h at -5 °C. The mixture was then quenched with a saturated solution of NaHCO3 (20 mL) and extracted with chloroform (30 mL × 3). The combined organic layer was washed with water, dried with anhydrous Na2SO4, and concentrated under reduced pressure to a residue. The residue was purified by silica gel column chromatography using hexane/ethyl acetate (5:1) as eluent. Yield: 0.69 g (78%). Rf 0.38. Mp 118-122 °C. 1H NMR (400 MHz, DMSO) δ 1.9-2.1 (m, 12H), 2.50 (s, 1H), 3.35 (s, 3H), 3.89 (dd, 2H, J = 2.8, 6.4 Hz), 4.01 (m, 1H), 4.41 (dd, 1H, J = 6.4, 6.4 Hz), 5.08 (dd, 1H, J = 2.0, 8.4 Hz), 5.33 (dd, 1H, J = 4.0, 6.8 Hz), 5.89 (d, 1H, J = 8.4 Hz), 6.31 (s, 1H), 7.14 (m, 2H), 8.10 (m, 4H). 13C NMR (100.6 MHz, DMSO) δ 20.31, 39.71, 55.68, 61.23, 67.62, 69.93, 70.82, 91.27, 100.88, 114.34, 132.16, 162.89, 169.92. MS (m/z): 614.99 (M+1)+. Anal. Calcd for C30H30O14: C, 58.63; H, 4.92. Found: C, 58.41; H, 5.06.

Reference： [1]Location in patent: experimental part Zacharia, James T.; Hayashi, Masahiko [Carbohydrate Research, 2012, vol. 348, p. 91 - 94]

54
[ 480-44-4 ]
[ 4163-45-5 ]
[ 80443-10-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With boron trifluoride diethyl etherate In dichloromethane at -20 - -5℃; Inert atmosphere; stereoselective reaction;	1.6. Synthesis of glycoside 4 Boron trifluoride etherate complex (0.027 g, 0.19 mmol, 0.13 equiv) was added to a stirred solution of glycosyl donor 3 (0.5 g, 1.43 mmol, 1.0 equiv), 2-p-methoxybenzyl-5,7-dihydroxychromone 2 (0.41 g, 1.43 mmol), and 10 equiv (by weight) of molecular sieves 4 Å in dichloromethane (5 mL) under argon atmosphere. The mixture was stirred for 1.5 h at -20 °C and then for a further 2 h at -5 °C. The mixture was then quenched with a saturated solution of NaHCO3 (20 mL) and extracted with chloroform (30 mL × 3). The combined organic layer was washed with water, dried with anhydrous Na2SO4, and concentrated under reduced pressure to a residue. The residue was purified by silica gel column chromatography using hexane/ethyl acetate (5:1) as eluent. Yield: 0.69 g (78%). Rf 0.38. Mp 118-122 °C. 1H NMR (400 MHz, DMSO) δ 1.9-2.1 (m, 12H), 2.50 (s, 1H), 3.35 (s, 3H), 3.89 (dd, 2H, J = 2.8, 6.4 Hz), 4.01 (m, 1H), 4.41 (dd, 1H, J = 6.4, 6.4 Hz), 5.08 (dd, 1H, J = 2.0, 8.4 Hz), 5.33 (dd, 1H, J = 4.0, 6.8 Hz), 5.89 (d, 1H, J = 8.4 Hz), 6.31 (s, 1H), 7.14 (m, 2H), 8.10 (m, 4H). 13C NMR (100.6 MHz, DMSO) δ 20.31, 39.71, 55.68, 61.23, 67.62, 69.93, 70.82, 91.27, 100.88, 114.34, 132.16, 162.89, 169.92. MS (m/z): 614.99 (M+1)+. Anal. Calcd for C30H30O14: C, 58.63; H, 4.92. Found: C, 58.41; H, 5.06.

Reference： [1]Location in patent: experimental part Zacharia, James T.; Hayashi, Masahiko [Carbohydrate Research, 2012, vol. 348, p. 91 - 94]

55
[ 99-96-7 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 3 h / Inert atmosphere; Reflux 2: thionyl chloride / 2 h / 60 °C 3: potassium carbonate / acetone / 24 h / 65 °C / Inert atmosphere

Reference： [1]Zacharia, James T.; Hayashi, Masahiko [Carbohydrate Research, 2012, vol. 348, p. 91 - 94]

56
[ 480-44-4 ]
[ 1389307-24-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; potassium carbonate / chloroform / 12 h / 45 °C / Inert atmosphere 2: water; ammonium hydroxide / methanol / 12 h / 20 °C

Reference： [1]Liu, Jidan; Chen, Ling; Cai, Shuanglian; Wang, Qiuan [Carbohydrate Research, 2012, vol. 357, p. 41 - 46]

57
[ 480-44-4 ]
acacetin-7-O-β-D-maltoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; potassium carbonate / chloroform / 12 h / 45 °C / Inert atmosphere 2: water; ammonium hydroxide / methanol / 12 h / 20 °C

Reference： [1]Liu, Jidan; Chen, Ling; Cai, Shuanglian; Wang, Qiuan [Carbohydrate Research, 2012, vol. 357, p. 41 - 46]

58
[ 480-44-4 ]
tilianin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; potassium carbonate / chloroform / 12 h / 45 °C / Inert atmosphere 2: water; ammonium hydroxide / methanol / 12 h / 20 °C

Reference： [1]Liu, Jidan; Chen, Ling; Cai, Shuanglian; Wang, Qiuan [Carbohydrate Research, 2012, vol. 357, p. 41 - 46]

59
[ 10236-47-2 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: pyridine; iodine / 2 h / 95 °C 2: sodium hydroxide / water / 6.5 h / 10 - 25 °C 3: sulfuric acid; water / 8 h / Reflux
	Multi-step reaction with 2 steps 1.1: pyridine; iodine / 2 h / 95 °C / Inert atmosphere 2.1: sodium hydroxide / water / 6 h / 10 - 25 °C 2.2: 8 h / Reflux

Reference： [1]Liu, Jidan; Chen, Ling; Cai, Shuanglian; Wang, Qiuan [Carbohydrate Research, 2012, vol. 357, p. 41 - 46]
[2]Current Patent Assignee: UNIV INNER MONGOLIA MEDICAL - CN108727446, 2018, A

60
2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide [ No CAS ]
[ 480-44-4 ]
[ 1389307-17-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With tetrabutylammomium bromide; potassium carbonate In chloroform at 45℃; for 12h; Inert atmosphere; regioselective reaction;	3.6. Synthesis of acacetin-7-O-β-d-acetylglucoside (9) Compound 9 was prepared from 18 and α-acetylglucose bromide as described for the preparation of 19 from 17 and α-acetylglucose bromide, yellow solid, yield: 83%. Mp 150-152 °C. 1H NMR (400 MHz, CDCl3) δ 12.85 (s, 1H, OH-5), 7.83 (d, J = 8.8 Hz, 2H, H-2', H-6'), 7.03 (d, J = 8.8 Hz, 2H, H-3', H-5'), 6.60 (s, 1H, H-3), 6.58 (d, J = 2.0 Hz, 1H, H-8), 6.44 (d, J = 2.0 Hz, 1H, H-6), 5.33 (d, J = 7.2 Hz, 1H, H-1), 5.31-5.28 (m, 1H, H-2), 5.20-5.14 (m, 2H, H-3,4), 4.32-4.19 (m, 2H, H-6), 3.98-3.95 (m, 1H, H-5), 3.90 (s, 3H, OCH3), 2.11-2.05 (m, 12H, 4 × CH3CO); 13C NMR (100 MHz, CDCl3) δ 20.3, 20.5, 20.6, 56.0, 61.3, 67.6, 71.0, 71.3, 72.1, 94.7, 96.4, 99.6, 102.6, 103.1, 105.2, 116.8, 120.2, 128.4, 156.8, 161.2, 161.3, 161.5, 164.1, 169.2, 169.5, 169.7, 169.8, 181.9; HRMS [M+Na]+ calcd for C30H30O14Na 637.5394, found 637.5381.
83.11%	With tetrabutylammomium bromide; potassium carbonate In chloroform at 45℃; for 12h;	S3 S3,Compound (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((5-Hydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro -2H-pyran-3,4,5-triyl triacetate(II)Synthesis Compound I (1.02 g, 3.59 mmol),Tetrabutylammonium bromide(1.84g, 6mmol),Acetyl bromide(2.94 g, 7.21 mmol) dissolved in chloroform (75 mL).K2CO3 (30 mL, 7.39 mmol, 0.25 mol/L) was added and refluxed for 12 h.Cooling the organic phase was separated, the aqueous phase was extracted with CH2C12, the combined organic phases were dried. Column chromatography to give the product 5.10g, yield 83.11%, m.p.142-144 .

Reference： [1]Location in patent: experimental part Liu, Jidan; Chen, Ling; Cai, Shuanglian; Wang, Qiuan [Carbohydrate Research, 2012, vol. 357, p. 41 - 46]
[2]Current Patent Assignee: UNIV INNER MONGOLIA MEDICAL - CN108727446, 2018, A Location in patent: Paragraph 0017; 0024; 0025

61
[ 3068-32-4 ]
[ 480-44-4 ]
[ 80443-10-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrabutylammomium bromide; potassium carbonate In chloroform at 45℃; for 12h; Inert atmosphere; regioselective reaction;	3.8. Synthesis of acacetin-7-O-β-d-acetylgalactoside (10) Compound 10 was prepared from 18 and α-acetylgalactose bromide as described for the preparation of 19 from 17 and α-acetylglucose bromide, yellow solid, yield: 75%. Mp 152-154 °C. 1H NMR (400 MHz, CDCl3) δ 12.82 (s, 1H, OH-5), 7.84 (d, J = 8.8 Hz, 2H, H-2', H-6'), 7.02 (d, J = 8.8 Hz, 2H, H-3', H-5'), 6.60 (s, 1H, H-3), 6.59 (d, J = 2.0 Hz, 1H, H-8), 6.45 (d, J = 2.0 Hz, 1H, H-6), 5.50 (d, J = 8.0 Hz, 1H, H-1), 5.42-5.49 (m, 1H, H-2), 5.19-5.13 (m, 2H, H-3,4), 4.26-4.20 (m, 1H, H-5), 4.17-4.08 (m, 2H, H-6), 3.90 (s, 3H, OCH3), 2.20-2.03 (m, 12H, 4 × CH3CO); 13C NMR (100 MHz, CDCl3) δ 20.0, 20.1, 20.3, 56.1, 61.4, 67.5, 71.1, 71.2, 72.5, 94.3, 96.4, 99.7, 102.5, 103.3, 105.4, 116.9, 120.1, 128.5, 156.9, 161.1, 161.2, 161.5, 164.2, 169.5, 169.6, 169.9, 169.4, 182.5; HRMS [M+Na]+ calcd for C30H30O14Na 637.5394, found 637.5377.

Reference： [1]Location in patent: experimental part Liu, Jidan; Chen, Ling; Cai, Shuanglian; Wang, Qiuan [Carbohydrate Research, 2012, vol. 357, p. 41 - 46]

62
C₂₈H₃₂O₁₄ [ No CAS ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
0.22 g	With sulfuric acid; water for 8h; Reflux;	3.4. Synthesis of acacetin (18)¹² (CH3O)2SO2 (2.3 mL, 24 mmol) was added dropwise to a stirred solution of rhoifolin (1.38 g, 2.4 mmol) in 3% aq NaOH (50 mL) at 10-25 °C for 30 min, then the reaction mixture was stirred for 6 h at the same temperature, and then concd H2SO4 (5 mL) was added to the mixture slowly. The mixture was heated under reflux for 8 h and then cooled to room temperature and filtered, the resulting precipitate was washed with saturated NaHCO3 and water and evaporated to dryness successively, and then the crude solid was chromatographed on silica gel using petroleum ether/ethyl acetate (3:1) as eluent to afford the yellow solid 0.22 g, yield: 32%. Mp 262-264 °C. (lit. 12, 260-262 °C). 1H NMR (400 MHz, DMSO-d6) δ 12.92 (s, 1H, OH-5), 10.86 (s, 1H, OH-7), 8.03 (d, J = 8.8 Hz, 2H, H-2', H-6'), 7.11 (d, J = 9.2 Hz, 2H, H-3', H-5'), 6.87 (s, 1H, H-3), 6.50 (d, J = 2.0 Hz, 1H, H-8), 6.20 (d, J = 2.0 Hz, 1H, H-6), 3.85 (s, 3H, OCH3); EIMS (m/z): 285 (M+1)+.

Reference： [1]Location in patent: experimental part Liu, Jidan; Chen, Ling; Cai, Shuanglian; Wang, Qiuan [Carbohydrate Research, 2012, vol. 357, p. 41 - 46]

63
α-hepta-O-acetyllactosyl bromide [ No CAS ]
[ 480-44-4 ]
[ 1389307-18-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	With tetrabutylammomium bromide; potassium carbonate In chloroform at 45℃; for 12h; Inert atmosphere; regioselective reaction;	3.10. Synthesis of acacetin-7-O-β-d-acetyllactoside (11) Compound 11 was prepared from 18 and α-acetyllactose bromide as described for the preparation of 19 from 17 and α-acetylglucose bromide, yellow solid, yield: 65%. Mp 98-100 °C. 1H NMR (400 MHz, CDCl3) δ 12.85 (s, 1H, OH-5), 7.81 (d, J = 8.8 Hz, 2H, H-2', H-6'), 7.00 (d, J = 8.8 Hz, 2H, H-3', H-5'), 6.58 (s, 1H, H-3), 6.54 (d, J = 2.4 Hz, 1H, H-8), 6.40 (d, J = 2.4 Hz, 1H, H-6), 5.38 (d, J = 7.2 Hz, 1H, H-1), 5.32 (t, J = 8.8 Hz, 1H, H-2), 5.22 (t, J = 9.2 Hz, 1H, H-3), 5.17-5.11 (m, 4H, H-4,5,6), 4.56 (d, J = 8.0 Hz, 1H, H-1), 4.20-4.10 (m, 3H, H-2, 3, 4), 3.96-3.90 (m, 3H, H-5, 6), 3.89 (s, 3H, OCH3), 2.18-1.99 (m, 21H, 7 × CH3CO) 2.17-1.98 (m, 21H, 7 × CH3CO); 13C NMR (100 MHz, CDCl3) δ 20.1, 20.3, 20.4, 21.3, 21.5, 21.8, 22.0, 58.9, 61.2, 64.6, 67.3, 68.7, 71.1, 72.2, 72.3, 73.2, 75.2, 76.4, 96.2, 96.3, 99.5, 102.8, 104.6, 104.7, 115.9, 123.1, 127.3, 157.8, 159.4, 163.5, 163.8, 165.7, 169.1, 169.2, 169.3, 169.5, 169.7, 170.5, 170.7, 181.3; HRMS [M+Na]+ calcd for C42H46O22Na 925.7894, found 925.7880.

Reference： [1]Location in patent: experimental part Liu, Jidan; Chen, Ling; Cai, Shuanglian; Wang, Qiuan [Carbohydrate Research, 2012, vol. 357, p. 41 - 46]

64
[ 480-44-4 ]
α-hepta-O-acetylmaltosyl bromide [ No CAS ]
acacetin-7-O-β-D-hepta-O-acetylmaltoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With tetrabutylammomium bromide; potassium carbonate In chloroform at 45℃; for 12h; Inert atmosphere; regioselective reaction;	3.12. Synthesis of acacetin-7-O-β-d-acetylmaltoside (12) Compound 12 was prepared from 18 and α-acetylmaltose bromide as described for the preparation of 19 from 17 and α-acetylglucose bromide, yellow solid, yield: 71%. Mp 118-120 °C. 1H NMR (400 MHz, CDCl3) δ 12.82 (s, 1H, OH-5), 7.84 (d, J = 8.8 Hz, 2H, H-2', H-6'), 7.02 (d, J = 8.8 Hz, 2H, H-3', H-5'), 6.61 (s, 1H, H-3), 6.57 (d, J = 2.0 Hz, 1H, H-8), 6.44 (d, J = 2.0 Hz, 1H, H-6), 5.44 (d, J = 7.6 Hz, 1H, H-1), 5.40-5.33 (m, 2H, H-2,3), 5.16-5.03 (m, 4H, H-4,5,6), 4.52 (d, J = 8.4 Hz, 1H, H-1), 4.31-4.24 (m, 2H, H-2, 3), 4.09-4.06 (m, 2H, H-4,5), 4.00-3.92 (m, 2H, H-6), 3.90 (s, 3H, OCH3), 2.12-2.02 (m, 21H, 7 × CH3CO) 2.17-1.98 (m, 21H, 7 × CH3CO); 13C NMR (100 MHz, CDCl3) δ 20.1, 20.2, 20.5, 21.2, 21.5, 21.7, 22.0, 59.7, 61.5, 64.7, 67.8, 69.6, 72.3, 72.4, 72.7, 73.1, 75.2, 76.5, 96.1, 96.2, 99.4, 102.5, 104.2, 104.4, 115.5, 123.1, 127.2, 157.4, 157.3, 163.1, 164.2, 166.6, 169.1, 169.3, 169.6, 169.8, 169.7, 170.1, 170.4, 182.1; HRMS [M+Na]+ calcd for C42H46O22Na 925.7894, found 925.7883.

Reference： [1]Location in patent: experimental part Liu, Jidan; Chen, Ling; Cai, Shuanglian; Wang, Qiuan [Carbohydrate Research, 2012, vol. 357, p. 41 - 46]

65
apigenin 7-O-neohesperidoside [ No CAS ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydroxide / water / 6.5 h / 10 - 25 °C 2: sulfuric acid; water / 8 h / Reflux

Reference： [1]Liu, Jidan; Chen, Ling; Cai, Shuanglian; Wang, Qiuan [Carbohydrate Research, 2012, vol. 357, p. 41 - 46]

66
[ 520-36-5 ]
[ 74-88-4 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; regiospecific reaction;
	With potassium carbonate In N,N-dimethyl-formamide for 2h;

Reference： [1]La Clair, James J. [Chemical Communications, 2018, vol. 54, # 21, p. 2611 - 2614]
[2]Coulerie, Paul; Nour, Mohammed; Maciuk, Alexandre; Eydoux, Cecilia; Guillemot, Jean-Claude; Lebouvier, Nicolas; Hnawia, Edouard; Leblanc, Karine; Lewin, Guy; Canard, Bruno; Figadere, Bruno [Planta Medica, 2013, vol. 79, # 14, p. 1313 - 1318]

67
4,6-bis(methoxymethyl)-2-(4-methoxylbenzoyloxy)acetophenone [ No CAS ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 4,6-bis(methoxymethyl)-2-(4-methoxylbenzoyloxy)acetophenone With potassium hydroxide In pyridine at 50℃; for 0.333333h; Stage #2: With acetic acid In pyridine; water for 0.5h; Stage #3: With hydrogenchloride In methanol Reflux;	Preparation of Flavones 4, 8 & 10 General procedure: To the esters 3 (1 mmol) in dry pyridine (1 ml) at 50 °C,powdered KOH (2 mmol) was added and reaction mixture was stirred vigorously for 20 min. The reaction mass was cooled, added to aqueous acetic acid (20 ml, 10%) and stirred for 30 min. It was extracted with diethyl ether (25 mlx 2) and washed with water (10 ml x 2), dried over anhydrous Na2SO4. On removal of solvent, diketones (containing some enol forms) were obtained as yellow solid products which gave green ferric reaction and were soluble in aq.NaOH (deep yellow solution). Compounds were identified by IR and UV spectral measurements (see Table S1 in supplementary information). The diketone/enol mixtures (200mg, without purification) were taken in methanolic HCl (20ml, 10%) and refluxed for 1-2 h till the completion of reaction(monitored by TLC solvent system, toluene 50: ethylacetate50: formic acid 10). Methanol was removed and reaction mass was poured into ice-water mixture, stirred for30 min, centrifuged; the separated flavones were purified through column chromatography using SiO2 and eluted in 2-3% methanol in chloroform. Compound 4 were crystallized from mixtures of chloroform/methanol. Yields, melting points and spectral properties are given below. Compounds were characterized by 1H NMR, UV and IR data.

Reference： [1]Pandurangan [Letters in Organic Chemistry, 2014, vol. 11, # 3, p. 225 - 229]

68
C₁₁H₁₄O₅ [ No CAS ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 0.17 h / 0 °C 1.2: 0 °C 2.1: pyridine / 20 °C 3.1: potassium hydroxide / pyridine / 0.33 h / 50 °C 3.2: 0.5 h 3.3: Reflux

Reference： [1]Pandurangan [Letters in Organic Chemistry, 2014, vol. 11, # 3, p. 225 - 229]

69
[ 121-98-2 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: thionyl chloride / chloroform; N,N-dimethyl-formamide / Reflux 2.1: pyridine / 20 °C 3.1: potassium hydroxide / pyridine / 0.33 h / 50 °C 3.2: 0.5 h 3.3: Reflux

Reference： [1]Pandurangan [Letters in Organic Chemistry, 2014, vol. 11, # 3, p. 225 - 229]

70
[ 480-44-4 ]
C₃₃H₂₈O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 14 h / 20 °C 2: N,N-diethylaniline / 3 h / 270 °C

Reference： [1]Lee, Phil Jun; Shin, Iljin; Seo, Seung-Yong; Kim, Hyoungsu; Kim, Hong Pyo [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 20, p. 4845 - 4849]

71
[ 480-44-4 ]
C₂₆H₂₂O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 14 h / 20 °C 2: N,N-diethylaniline / 3 h / 270 °C 3: boron trichloride / dichloromethane; n-heptane / 2 h / 0 - 20 °C

Reference： [1]Lee, Phil Jun; Shin, Iljin; Seo, Seung-Yong; Kim, Hyoungsu; Kim, Hong Pyo [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 20, p. 4845 - 4849]

72
C₂₀H₂₂O₅ [ No CAS ]
[ 480-44-4 ]
C₃₃H₂₈O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 14h;	Representative Procedure for Preparation of Chrysin Analogues General procedure: To a solution of chrysin (8.89 g, 34.97 mmol) and carbonate A (11.97 g, 34.97 mmol) in THF/DMF (2:1, total 60 mL) were added K2CO3 (9.67 g, 69.9 mmol) and (Ph3P)4Pd, (404.4 mg, 0.350 mmol) at room temperature and the resulting mixture was stirred for 14h. The reaction mixture was acidified with 1 N HCl, and diluted with Et2O to form yellow precipitate. The yellow precipitate was collected by filtration, and washed sequentially with cold (0 °C) H2O and Et2O to afford aryl allyl ether 4A (16.63 g, 94%). A solution of aryl allyl ether 4A (4.521 g, 8.923 mmol) in diethylaniline (100 mL) was stirred for 3 h at 270 °C. The reaction mixture was allowed to cool to room temperature, concentrated invacuo, and purified by column chromatography (silica gel; hexanes/EtOAc, 4/1 to 2/1) to afford 4B (3.672g, 81%)

Reference： [1]Lee, Phil Jun; Shin, Iljin; Seo, Seung-Yong; Kim, Hyoungsu; Kim, Hong Pyo [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 20, p. 4845 - 4849]

73
C₃₇H₃₈O₁₆ [ No CAS ]
[ 50-99-7 ]
[ 7400-08-0 ]
rhamnose [ No CAS ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In methanol; water at 100℃; for 2h;	3.4 Acid hydrolysis Complete acid hydrolysis was performed by treating 3 mg of each isolated glycoside with a few drops of 1.5 N HCl in aqueous methanol for 2 h at 100 °C. Hydrolysate was then separately extracted with successive portions of ethyl acetate. The solvent was evaporated under reduced pressure, and the residue (containing the aglycone) was dissolved in suitable solvent and subjected to TLC investigation alongside authentic aglycones. The mother liquor was neutralized with sodium bicarbonate and filtered. The precipitate on the filter paper was washed with distilled water. The filtrate and washings were combined, then evaporated under reduced pressure to obtain a residue (sugar moiety). The residue was dissolved in few drops of isopropanol and eluted on Whatman filter paper No. 1 alongside authentic sugars using system II as solvent system.

Reference： [1]Abdallah, Hossam M.; Almowallad, Fahad M.; Esmat, Ahmed; Shehata, Ibrahim A.; Abdel-Sattar, Essam A. [Phytochemistry Letters, 2015, vol. 13, p. 74 - 80]

74
[ 17176-77-1 ]
[ 480-44-4 ]
C₃₀H₂₅O₈P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With triethylamine In tetrachloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 1h;	1 Compound B-1 Compound B-1 To a solution of acacetin (3 g, 10.5 mmol) and 4.5 mL of NEt3 (32 mmol) in DMF (20 mL) at 0° C., 3.05 g of dibenzyl phosphite (11.6 mmol) in CCl4 (5.5 mL) was added dropwise and the mixture was stirred for 1 h at room temperature. The mixture was evaporated and the crude product was purified by column chromatography over silica gel by using n-hex/EtOAc/CH2Cl2 (6:1:2 v/v). After evaporating the solvent, 1.3 g of yellow solid of B-1 was obtained. Compound B-1: Yellow Solid. Yield 54%. C30H25O8P (544.49). EI-MS: m/z 545.14 [M]. 1H NMR (400 MHz, CDCl3): δ=12.81 (s, 1H), 7.83 (d, J=8.8 Hz, 2H), 7.03 (d, J=8.8 Hz, 2H), 6.84 (s, 1H), 6.62 (s, 1H), 6.54 (s, 1H), 5.19 (s, 2H), 5.17 (s, 2H), 3.91 (s, 3H) ppm.

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF HONG KONG - US2015/218193, 2015, A1 Location in patent: Paragraph 0222-0224

75
[ 480-44-4 ]
[ 229625-50-7 ]
C₂₅H₃₁O₉P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.1 g	With caesium carbonate; sodium iodide In N,N-dimethyl-formamide	1 Compound C-2 Compound C-2 To a solution of acacetin (4.5 g, 15.8 mmol) in DMF (35 mL), 4.1 mL of chloromethyl ditertbutyl phosphate (20.6 mmol), 6.1 g of caesium carbonate (31.6 mmol) and 0.25 g of sodium iodide (0.1 eq) were added. After stirring the reaction mixture over night, the mixture was extracted with 0.5M TBME/phosphate buffer (pH=7) and preparative HPLC was carried out using 85% MeOH/15% H2O. After evaporating the solvent, 4.1 g of a light yellow solid was obtained. 2.1 g of the yellow solid was dissolved in dichloromethane (35 mL) and 35 mL of tetrafluoroacetic acid was then added slowly. After stirring for 10 to 20 min, the reaction mixture was evaporated at low temperature. The crude product was washed with acetonitrile (30 mL) twice and was dried. 3.2 g of a light yellow solid of C2 was obtained. Compound C-2: Light yellow solid. Yield 51%. C17H15O9P (394.27). EI-MS: m/z 395 [M+], 297 [M+H-OP(O)(OH)2]+. 1H NMR (200 MHz, DMSO-d6): δ=12.8 (bs, 1H), 8.04 (d, J=9 Hz, 2H), 7.08 (d, J=9 Hz, 2H), 6.87 (s, 1H), 6.83 (d, J=6 Hz, 2H), 6.47 (d, J=3 Hz, 1H), 5.66 (s, 1H), 5.60 (s, 1H), 3.84 (s, 3H) ppm. 13C NMR (200 MHz, d6-DMSO): δ=182.82, 164.57, 163.25, 162.72, 162.01, 157.69, 129.15, 123.31, 115.33, 106.40, 104.49, 100.08, 95.29, 87.96, 56.34 ppm 31P NMR (200 MHz, d6-DMSO): δ=-1.56 ppm.

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF HONG KONG - US2015/218193, 2015, A1 Location in patent: Paragraph 0232-0234

76
[ 480-44-4 ]
C₁₆H₁₃O₈P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 1H-tetrazole / acetonitrile / 12 h / 20 °C 1.2: 0.08 h / 20 °C 2.1: formic acid; palladium 10% on activated carbon / methanol; tetrahydrofuran / 4 h / 760.05 Torr
	Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide; tetrachloromethane / 1 h / 0 - 20 °C 2: formic acid; palladium 10% on activated carbon / methanol; tetrahydrofuran / 4 h / 760.05 Torr

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF HONG KONG - US2015/218193, 2015, A1
[2]Current Patent Assignee: THE UNIVERSITY OF HONG KONG - US2015/218193, 2015, A1

77
[ 480-44-4 ]
C₁₆H₁₁O₈P^(2-)*2Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 1H-tetrazole / acetonitrile / 12 h / 20 °C 1.2: 0.08 h / 20 °C 2.1: formic acid; palladium 10% on activated carbon / methanol; tetrahydrofuran / 4 h / 760.05 Torr 3.1: sodium hydroxide / water / pH 10
	Multi-step reaction with 3 steps 1: triethylamine / N,N-dimethyl-formamide; tetrachloromethane / 1 h / 0 - 20 °C 2: formic acid; palladium 10% on activated carbon / methanol; tetrahydrofuran / 4 h / 760.05 Torr 3: sodium hydroxide / water / pH 10

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF HONG KONG - US2015/218193, 2015, A1
[2]Current Patent Assignee: THE UNIVERSITY OF HONG KONG - US2015/218193, 2015, A1

78
[ 480-44-4 ]
C₁₇H₁₅O₉P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate; sodium iodide / N,N-dimethyl-formamide 2: trifluoroacetic acid / dichloromethane

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF HONG KONG - US2015/218193, 2015, A1

79
[ 480-44-4 ]
(x)C₆H₁₅N*C₁₆H₁₃O₈P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triethylamine / N,N-dimethyl-formamide; tetrachloromethane / 1 h / 0 - 20 °C 2.1: chloro-trimethyl-silane / dichloromethane / 1 h / 20 °C 2.2: 0.25 h
	Multi-step reaction with 2 steps 1.1: 1H-tetrazole / acetonitrile / 12 h / 20 °C 1.2: 0.08 h / 20 °C 2.1: chloro-trimethyl-silane / dichloromethane / 1 h / 20 °C 2.2: 0.25 h

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF HONG KONG - US2015/218193, 2015, A1
[2]Current Patent Assignee: THE UNIVERSITY OF HONG KONG - US2015/218193, 2015, A1

80
[ 480-44-4 ]
[ 108549-23-1 ]
C₃₀H₂₅O₈P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one; Dibenzyl N,N-diisopropylphosphoramidite With 1H-tetrazole In acetonitrile at 20℃; for 12h; Stage #2: With tert.-butylhydroperoxide In acetonitrile at 20℃; for 0.0833333h;	1 Compound A-1 Compound A-1 To an acetonitrile (35 mL) solution of acacetin (4 g, 14.1 mmol) was added 1.1 g of tetrazole (15.51 mmol) and 5.4 g of dibenzyl N,N-diisopropylphosphoramidite (15.51 mmol). After 12 h of stirring at room temperature, 9.75 mL of 70% of 1,1-dimethylethyl hydroperoxide in water was added and stirred for 5 min under room temperature. The mixture was extracted with 0.5M TBME/phosphate buffer (pH=7) and preparative HPLC was carried out by using 90% acetonitrile/10% H2O. After evaporating the solvent, 5.8 g of yellow solid of compound A-1 was obtained. Compound A-1: Yellow Solid. Yield 76%. C30H25O8P (544.49). EI-MS: m/z 545.14 [M]. 1H NMR (400 MHz, CDCl3): δ=12.81 (s, 1H), 7.83 (d, J=8.8 Hz, 2H), 7.03 (d, J=8.8 Hz, 2H), 6.84 (s, 1H), 6.62 (s, 1H), 6.54 (s, 1H), 5.19 (s, 2H), 5.17 (s, 2H), 3.91 (s, 3H) ppm.

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF HONG KONG - US2015/218193, 2015, A1 Location in patent: Paragraph 0215-0217

81
[ 20633-93-6 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With ethanol; sulfuric acid for 2h; Reflux;	2.5. 5,7-Dihydroxy-4'-methoxyflavone (acacetin, 1a) To a solution of 1f (101 mg, 0.170 mmol) in ethanol (1.70 mL) was added conc. sulfuric acid (170 μL). The mixture was heated under reflux for 2 h, then the reaction was cooled at 0 °C. The resulting precipitates were recovered by filtration and washed with water to afford 1a (42 mg, 87%) as yellow solid. This was recrystallized from methanol to give an analytical sample of 1a as yellow needles, mp 256.0-257.8 °C [lit. [3] mp 254.6-257.5 °C]; 1H NMR δ(DMSO-d6): 3.84 (s, 3H, -OMe), 6.18 (d, J = 2.2 Hz, 1H, H-6), 6.49 (d, J = 2.0 Hz, 1H, H-8), 6.86 (s, 1H, H-3), 7.10 (d, J = 9.0 Hz, 2H, H-3,H-5), 8.02 (d, J = 9.0 Hz, 2H, H-2, H-6), 10.86 (s, 1H, OH-7), 12.91 (s, 1H, OH-5); 13C NMR (DMSO-d6): δ 55.58, 94.06, 98.91, 103.56, 103.78, 114.61, 122.84, 128.36, 157.36, 161.46, 162.33, 163.33, 164.24, 181.81; the signals 114.61 and 128.36 included two carbons.

Reference： [1]Hanamura, Shun; Hanaya, Kengo; Shoji, Mitsuru; Sugai, Takeshi [Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 128, p. 19 - 26]

82
[ 108-73-6 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: zinc(II) chloride / diethyl ether / 0 - 5 °C 1.2: 6 h / 0 - 5 °C 2.1: hydrogenchloride / water / 8 h / 20 °C 3.1: potassium hydroxide / ethanol / 3 h / 20 °C 3.2: 1 h / 55 °C
	Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / ethyl acetate / 10 h / 50 °C 2.1: potassium carbonate / acetone / 0.17 h / 20 °C / Inert atmosphere 2.2: 24 h / 60 °C / Inert atmosphere

Reference： [1]Jiang, Wen-Jun; Daikonya, Akihiro; Ohkawara, Mitsuyoshi; Nemoto, Takashi; Noritake, Ryusuke; Takamiya, Tomoko; Kitanaka, Susumu; Iijima, Hiroshi [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 1 - 5]
[2]Current Patent Assignee: UNIVERSITY OF SHANGHAI FOR SCIENCE AND TECHNOLOGY - CN107033112, 2017, A

83
[ 110865-03-7 ]
[ 123-11-5 ]
[ 480-44-4 ]

Yield	Reaction Conditions	Operation in experiment
17.8%	Stage #1: 2-chloro-1-(2,4,6-trihydroxyphenyl)ethan-1-one; 4-methoxy-benzaldehyde With potassium hydroxide In ethanol at 20℃; for 3h; Stage #2: With hydrogenchloride In ethanol; water at 55℃; for 1h;	2.5.1. Acacetin (27) KOH (250 mg, 4.47 mmol) ethanol solution (10 mL) was added to a solution of 26 (300 mg, 1.49 mmol) in EtOH (10 mL). Then, 4'-methoxy benzaldehyde (202 mg, 1.49 mmol) was added to the reaction mixture solution and stirred at room temperature for 3 h. Five milliliters of aqueous HCl (10 M) was added and stirred at 55 °C for 1 h. EtOH was removed under a vacuum. Distilled water was added to the residue, and the mixture was extracted with EtOAc three times. The organic layer was combined and dried over Na2SO4. The filtered EtOAc layer was evaporated to give a red-yellow oil that was purified by silica gel column chromatography eluting with MeOH and CHCl3 to give 27 as a yellow powder (75 mg, 17.8% yield).

Reference： [1]Jiang, Wen-Jun; Daikonya, Akihiro; Ohkawara, Mitsuyoshi; Nemoto, Takashi; Noritake, Ryusuke; Takamiya, Tomoko; Kitanaka, Susumu; Iijima, Hiroshi [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 1 - 5]

84
[ 480-44-4 ]
C₁₆H₁₀Br₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-Bromosuccinimide In trifluoroacetic acid at 20℃; for 5h;	3.1; 3.2; 3.3; 3.4; 3.5 Preparation of 5,7-dihydroxy-6,8-dibromo-4'-methoxyflavone IV Step 3-1, 35.4 mmol (10 g) of 5,7-dihydroxy-4'-methoxyflavone III and 100 ml of trifluoroacetic acid were weighed, addedInto the third three-necked flask, and then weighed 70.9mmol (12.6g) NBS slowly added to a third three-necked flask to obtain a mixed solution III.Step 3-2, the mixture III was stirred at room temperature for 5 hours to obtain the reaction solution III.Step 3-3, the reaction solution was poured into ice water, precipitated to give a solid .Step 3-4, the solid II was filtered and washed with water to obtain a green cake II.In steps 3-5, the filter cake II was subjected to column chromatography using a solution of ethyl ether: ethyl acetate = 4: 1 in a volume ratio to obtain 14.5 g of a yellow solid.

Reference： [1]Current Patent Assignee: UNIVERSITY OF SHANGHAI FOR SCIENCE AND TECHNOLOGY - CN107033112, 2017, A Location in patent: Paragraph 0036; 0037; 0038; 0039; 0040; 0041

85
[ 480-44-4 ]
N-(3-bromopropyl)propane-1-sulfonamide [ No CAS ]
N-{3-[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxochroman-3-yl]propyl}propane-1-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: N-(3-bromopropyl)propane-1-sulfonamide With magnesium In tetrahydrofuran Heating; Stage #2: 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one With zirconocene dichloride In tetrahydrofuran at 30 - 40℃; for 2h;	1 Example 1 Preparation of N-{3-[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxochroman-3-yl]propyl}propane-1-sulfonamide ( Compound 1) N-(3-bromopropyl)propane-1-sulfonamide (2.9 g, 12 mmol) was dissolved in 100 mL of dry tetrahydrofuran and added dropwise with stirring to fresh magnesium shavings (0.30 g, 12.5mmol), 1 iodine flask, a small drop first, and then gradually drip Grignard reaction after about 20min dripping finished, and then stirred back to the magnesium turnings basically completely dissolved, stop heating, Grignard reagent to be cooled to 30 ~ 40 ° C, the catalyst was added zirconocene zirconium (0.15g, 0.5 mmol) and 5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one (2.8 g, 10.0 mmol) were added and the reaction was refluxed for 2 h. After the reaction was completed, the reaction solution was cooled to room temperature, then saturated aqueous NH4Cl (100 mL) was added, extracted with petroleum ether (100 mL x 3) and dried over anhydrous Na2SO4. Drying under reduced pressure was performed by silica gel column chromatography (toluene-dichloromethane: 1: 9), and the product-containing fraction was collected. The solvent was evaporated to dryness to afford a white solid N-{3-[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxochroman-3-yl]propyl}propane-1-sulfonamide 2.9 g, yield 65%.

Reference： [1]Current Patent Assignee: UNIV MUDANJIANG MEDICAL - CN106831686, 2017, A Location in patent: Paragraph 0040; 0041; 0042; 0043; 0044

86
[ 4227-95-6 ]
[ 480-44-4 ]
¹³C-4’,¹²C-7-methylapigenenin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; regiospecific reaction;

Reference： [1]La Clair, James J. [Chemical Communications, 2018, vol. 54, # 21, p. 2611 - 2614]

87
[ 480-44-4 ]
[ 106-96-7 ]
7-O-propargylacacetin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate In acetone for 2h; Reflux;

Reference： [1]Wang, Gang-Qiang; Yan, Li-Li; Wang, Qiu-An [Heterocyclic Communications, 2018, vol. 24, # 2, p. 119 - 124]

88
[ 480-44-4 ]
[ 142-61-0 ]
5,7-di-O-hexanoyl-acacetin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With dmap; triethylamine In N,N-dimethyl-formamide at 20℃; for 4.5h; Cooling with ice;	General procedure for the synthesis of perhexanoylated flavonoid (1a-7a) General procedure: Flavonoid (1 (5.40 g, 0.02 mol), 2 (5.72 g, 0.02 mmol), 3 (5.45 g, 0.02 mmol), 4 (5.69 g, 0.02 mmol), 5 (5.08 g, 0.02 mmol), 6 (5.40 g, 0.02 mmol), or 7 (6.04 g, 0.02 mmol)) was dissolved in DMF (50 mL); Et3N (for 4, 5, 6.9 mL, 0.05 mol; for 1, 3, 6, 9.7 mL, 0.07 mol; for 2, 12.4 mL, 0.09 mol; for 7, 15.3 mL, 0.11 mol) and DMAP (240 mg, 2 mmol) were added. The mixture was then cooled in an ice-bath, and hexanoyl chloride (for 4, 5, 6.9 mL, 0.05 mol; for 1, 3, 6, 9.7 mL, 0.07 mol; for 2, 12.4 mL, 0.09 mol; for 7, 15.3 mL, 0.109 mol) was added and the reaction was allowed to slowly rise to room temperature in 30 min and stirred for an additional 4 h. After complete consumption of the flavonoid starting material as shown by TLC, the reaction mixture was diluted with CH2Cl2 (100 mL) and washed with 1 M HCl aqueous solution (100 mL), saturated aqueous NaHCO3 (100 mL * 2), brine (100 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford the crude product (oil/solid), which was further purified by crystallization (methanol). Compound 1a-3a (1a, 9.8 g, 87%, Ref. [30]; 2a, 11.5 g, 85%; 3a, 10.4 g, 92%) were obtained as a light yellow solid and 4a-7a (4a, 8.4 g, 87%; 5a, 8.6 g, 95%, Ref. [28]; 6a, 9.1 g, 81%, Ref. [43]; 7a, 13.1 g, 83%) as a white solid. Analytical data and NMR spectra see Supporting Information.
	With dmap; triethylamine In N,N-dimethyl-formamide

Reference： [1]Zheng, Zhiwei; Han, Ziyi; Cai, Li; Zhou, Dandan; Chavis, Bryson R.; Li, Changsheng; Sui, Qiang; Jiang, Kaiyuan; Gao, Qi [Tetrahedron Letters, 2018, vol. 59, # 50, p. 4442 - 4447]
[2]Han, Ziyi; Zheng, Zhiwei; Cai, Li; Zhou, Dandan; Li, Changsheng; Sui, Qiang; Liu, Shuai; Gao, Qi [Tetrahedron Letters, 2018, vol. 59, # 42, p. 3773 - 3776]

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CAS No. :	480-44-4	MDL No. :	MFCD00016936
Formula :	C₁₆H₁₂O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DANYIYRPLHHOCZ-UHFFFAOYSA-N
M.W :	284.26	Pubchem ID :	5280442
Synonyms :	5,7-Dihydroxy-4'-methoxyflavone;LY064233;Acacetin. NSC 76061.;NSC 76061

Num. heavy atoms :	21
Num. arom. heavy atoms :	16
Fraction Csp3 :	0.06
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	2.0
Molar Refractivity :	78.46
TPSA :	79.9 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.66 cm/s

Log Po/w (iLOGP) :	2.56
Log Po/w (XLOGP3) :	3.35
Log Po/w (WLOGP) :	2.88
Log Po/w (MLOGP) :	0.77
Log Po/w (SILICOS-IT) :	3.03
Consensus Log Po/w :	2.52

[ CAS No. 480-44-4 ] {[proInfo.proName]}

Quality Control of [ 480-44-4 ]

Related Doc. of [ 480-44-4 ]

Product Details of [ 480-44-4 ]

Calculated chemistry of [ 480-44-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 480-44-4 ]

Application In Synthesis of [ 480-44-4 ]

[ 480-44-4 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Log S (ESOL) :	-4.14
Solubility :	0.0204 mg/ml ; 0.0000717 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.71
Solubility :	0.0056 mg/ml ; 0.0000197 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.1
Solubility :	0.00225 mg/ml ; 0.00000791 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.98

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling