* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Phytochemistry, 1996, vol. 43, # 2, p. 393 - 395
[2] Journal of Natural Products, 2004, vol. 67, # 3, p. 407 - 410
[3] Patent: US9314438, 2016, B2, . Location in patent: Page/Page column 26; 27
4
[ 29584-19-8 ]
[ 27975-19-5 ]
Reference：
[1] Journal of Organic Chemistry, 1955, vol. 20, p. 884,895
[2] Journal de Pharmacie et de Chimie, 1931, vol. <8> 14, p. 321,325, 369, 372[3] Bulletin de la Societe de Chimie Biologique, 1931, vol. 13, p. 781,785, 790
[4] Food Chemistry, 2016, vol. 190, p. 270 - 275
Reference：
[1] Journal de Pharmacie et de Chimie, 1931, vol. <8> 14, p. 321,325, 369, 372[2] Bulletin de la Societe de Chimie Biologique, 1931, vol. 13, p. 781,785, 790
9
[ 50-99-7 ]
[ 7664-93-9 ]
[ 57817-89-7 ]
[ 27975-19-5 ]
Reference：
[1] Journal de Pharmacie et de Chimie, 1931, vol. <8> 14, p. 99,100[2] Bulletin de la Societe de Chimie Biologique, 1931, vol. 13, p. 636,645, 656
With sodium tetrahydroborate; In ethanol; at 0℃; for 2h;
To a solution of <strong>[27975-19-5]isosteviol</strong> 1 (31.8 g, 0.1 mol) in EtOH (200 mL) was added NaBH4 (5.7 g, 0.15 mol) slowly at 0 C. The mixture was stirred for 2 h. Then mixture was quenched with a saturated NH4Cl aqueous solution. After that, the reaction mixture was concentrated under vacuum, and extracted with CH2Cl2 and H2O. The organic layer was washed with saturated NaCl aqueous solution, dried with MgSO4 and concentrated under vacuum to give white powder, then recrystallized from EtOH-H2O (1:1) to afford compound 3 as a colourless crystal (30.1 g, 94%), m.p. 188.6-190.5 C; X-ray crystal file is available from the Cambridge Crystallographic Data Centre: CCDC 1577013; IR (KBr): 3474, 2989, 2946, 2894, 1702, 1649, 1452, 1252, 1187, 1056 cm-1; 1H NMR (400 MHz, CD3OD): delta 3.78 (dd, J=4.4 Hz, 1H), 2.10 (d, J=13.1 Hz, 1H), 1.20-1.95 (m, 14H), 1.16 (s, 3H), 0.92-1.14 (m, 5H), 0.88 (s, 3H), 0.85 (s, 3H); 13C NMR (100 MHz, CD3OD): delta 181.7, 81.0, 58.4, 57.4, 56.6, 44.6, 43.6, 43.2, 43.1, 43.0, 41.3, 39.3, 39.2, 35.0, 29.6, 25.4, 23.0, 21.4, 20.1, 14.0; HRMS (ESI, m/z) calculated for C20H31O3 [M-H]-: 319.2273; found: 319.2274.
137 mg
With sodium tetrahydroborate; In tetrahydrofuran; at 20℃; for 1h;
To a solution of compound 1 (150 mg) in THF (2 ml) was added NaBH4 (50 mg). After stirring at ambient temperature for 1 h, water was added and the solution was extracted with EtOAc. The EtOAc layer was washed with water, dried over anhydrous Na2SO4 and the solvent was evaporated in vacuo. The crude product was purified by column chromatography using CH2Cl2-MeOH (95:5) to give 2 (137 mg). Spectroscopic (1H NMR and ESMS) data were in agreement with the structure and the NMR data were consistent with the reported values [18-20].
Chemical: Compound A, (ent-17-norkaurane-16-oxo-18-oic acid, molecular formula, C20H40O3, Molecular weight: 318.5) is produced from stevioside through acidic hydrolysis, crystallization and purification. The structure of compound A are confirmed by inferred analysis and NMR, which are consistence with previously published data. The purity of compound A is greater than 99% determined by high performance liquid chromatograph.
With sulfuric acid; at 60 - 70℃; for 6h;
Preparation of ADIS The pulverized, dry S. rebaudina leaves were successively extracted with n-hexane, ethyl acetate, and methanol. The methanol extract was subjected to silica column chromatography to yield stevioside. ADIS was obtained from stevioside as described previously ( Wonganan et al., 2013 ). Briefly, stevioside was dissolved in 20% sulfuric acid solution and then heated at 60-70 C for 6 h with stirring. The mixture was extracted with ethyl acetate.
With sulfuric acid;Heating;
stevioside(4.0 g) in a round bottom flask.It was dissolved by adding 10% H 2 SO 4 and stirred under heating.After completion of the reaction, the system was cooled to room temperature, filtered, and washed with water to give Compound 2 as a white solid.
With sulfuric acid; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; at 0 - 20℃; for 48h;
<strong>[27975-19-5]Isosteviol</strong> (500 mg, 1.57 mmol) and mCPBA (540 mg, 2.36 mmol) were dissolved in the mixed solution of dichloromethane and methanol [10 mL, 1:1 (V/V)]. To the solution, 0.5 mL of concentrated sulfuric acid were added dropwise over several minutes, then stirred at room temperature (r.t.). Two days later, the solution was poured into 40 mL of water, and adjusted to neutrality, then extracted with CH2Cl2 (3 × 30 mL). The combined organic layer was washed with water and saturated brine sequentially, dried by anhydrous sodium sulfate overnight. After filtration, the filtrate was evaporated to dryness in vacuo, and the crude product was purified by rapid chromatography [EtOAc/petroleum ether = 1/2 (V/V)] to give 2 (310mg, 59%) as white solid.
With potassium hydroxide; In dimethyl sulfoxide; at 20℃;
The ethyl ent-16-oxobeyeran-19-oate 2 was obtained by treating <strong>[27975-19-5]isosteviol</strong> with CH3CH2Br and KOH in DMSO at room temperature in good yield according to the literature method [48] . Yield 98%; Mp 124.7-127.4 C; IR (KBr): 2958, 2927, 2843, 1727, 1465, 1445, 1379, 1320, 1257, 1226, 1151, 1128, 1094, 1055, 1023, 974, 926, 872, 773, 587, 505 cm-1; 1H NMR (400 MHz, CDCl3, ppm): delta 4.10 (q, J = 7.12 Hz, 2H), 2.96 (dd, J = 18.46, 3.14 Hz, 1H), 2.17 (d, J = 13.32 Hz, 1H), 1.99 (d, J = 18.86 Hz, 1H), 1.88-1.58 (m, 8H), 1.47-1.33 (m, 6H), 1.26 (t, J = 7.12 Hz, 3H), 1.22-1.19 (m, 2H), 1.18 (s, 3H), 1.07 (s, 3H), 1.05-0.86 (m, 1H), 0.77 (s, 3H); HRMS (ESI, m/z) calcd for C22H34O3Na [M + Na]+ 369.2406. Found: 369.2400.
96%
With potassium hydroxide; In dimethyl sulfoxide; at 25℃; for 4h;
To a solution of <strong>[27975-19-5]isosteviol</strong> 1 (31.8 g, 0.1 mol) in DMSO (100 mL) was added EtBr (16.3 g, 11.2 mL, 0.15 mol) and KOH (8.4 g, 0.15 mol) at 25 C. After stirring for 4h, the mixture was added into 1000 mL ice water to precipitate white powder. Then filtration through buchner funnel, the white powder was washed with water and recrystallized from EtOH to afford compound 2 as a colourless crystal (33.3 g, 96%), m.p. 122.2-122.8 C; X-ray crystal file is available from the Cambridge Crystallographic Data Centre: CCDC 1577012; IR (KBr): 2956, 2928, 2845, 1728, 1465, 1380, 1227, 1151, 1095, 1026 cm-1; 1H NMR (400 MHz, CDCl3): delta 4.11 (q, J = 7.0 Hz, 2H),2.65 (dd, J = 18.5, 3.2 Hz, 1H), 2.19 (d, J = 13.3 Hz, 1H), 2.04-1.33 (m, 14H), 1.27 (t, J = 7.1 Hz, 3H), 1.23-1.21 (m, 1H), 1.2 (s, 3H), 1.16-1.0 (m, 2H), 0.99 (s, 3H), 0.97-0.86 (m, 1H), 0.73 (s, 3H); 13C NMR (100 MHz, CDCl3): delta 222.5, 177.3, 60.0, 57.0, 54.7, 54.3, 48.7, 48.5, 43.7, 41.6, 39.9, 39.5, 38.0, 37.9, 37.3, 28.9, 21.7, 20.3, 19.9, 19.0, 14.1, 13.4; HRMS (ESI, m/z) calculated for C22H35O3 [M+H]+: 347.2586; found: 347.2575.
Weigh 18g of isostrinAnd 15gK0H,Added to lOOmlDMSO,Stirring lOmin,Add 6mlC2H5Br and a small amount of crown ether,40 C reaction 4h, after the end of the reaction to room temperature,The reaction solution was poured into 1000 ml of cold water, left for 30 min,Filtration, precipitation washed 3 times
In a 100 ml round bottom flask were added 3.18 g (10 mmol) of compound (IV) in this order,2.000 g (50 mmol) of NaOH,Then add 15ml of water, 10ml of ethanol, stirring 5 minutes, then add 5ml 37% formaldehyde solution, set the oil bath temperature 60 C, stirring reaction 5h. After completion of the reaction, the mixture was neutralized to pH = 7 with 10 wt% hydrochloric acid and a large amount of white flocculent solid was formed. A large amount of white solid was collected by filtration and recrystallized from methanol to obtain 3.185 g of white needle crystals. Yield: 91%
With sodium; In ethanol; water; at 50℃; for 3h;
Take 250mL of anhydrous ethanol in a 500mL reaction flask, add 6.0g of metal sodium, until the metal sodium completely react, add 9.8g of compound 1, magnetic stirring, the system temperature to 50?C, then add 20mL formaldehyde aqueous solution, continue to reaction 3 Hour to TLC follow the end of the reaction. The reaction system was poured into 500mL distilled water. The system was adjusted to pH 5 with dilute hydrochloric acid. The system had a large amount of white flocculent precipitate. The crude product was filtered and dried to obtain 10 g of crude product of compound 2, which was used for the next reaction without separation and purification.
With sodium hydroxide; In ethanol; at 20℃; for 5h;
Weighed compound 2 (10g), dissolved in ethanol (50mL), and added NaOH solution (2g) and HCHO solution at room temperature.(6.6 mL), reaction for 5 h.The reaction was monitored by the spot plate. After the reaction was completed, water was added, ethyl acetate was extracted, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, filtered and evaporated.Purified by column chromatography,Compound 10 was obtained.
With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 20℃; for 8h;
General procedure: To a solution of compound 1a (0.12 g, 0.361 mmol) in DMF (0.90 mL) was added benzyl bromide (0.077 mL, 0.119 mmol), potassium carbonate (0.25g, 1.800 mmol) and a catalytic amount of potassium iodide. The mixture was stirred at room temperature for 8 h and poured into brine followed by extracted with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure. The residue was purified by column chromatography (petroleum ether-ethyl acetate, 2.8:1) to give 1b as a white solid (0.12 g, 78.71%).
10 g of stevioside (X) and 600 mL of 10wt% dilute sulfuric acid solution were placed in a 1000 mL round bottom flask, stirred in oil bath 75 C, reacted for 1 h and a small amount of yellow flocculent solid was produced. The reaction was continued for 4h. The reaction was stopped, cooled to room temperature, filtered, the yellow solid obtained by suction filtration was transferred to a 100 mL single-necked flask and recrystallized from acetone. The resulting mixture was cooled, white crystals were slowly precipitated, filtered and dried to obtain compound (XI) 2.98 g. Yield: 65.1%.
3,5-dinitrobenzyl (-)-ent-16-oxobeyeran-19-oate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
61%
With triethylamine; In N,N-dimethyl-formamide; at 25℃; for 16h;
To a solution of (-)-isosteviol 1 (3.09 g, 9.7 mmol) in DMF (20 mL), triethylamine (2.3 mL, 17.1 mmol) and <strong>[74367-78-5]3,5-dinitrobenzyl chloride</strong> (2.1 g, 9.7 mmol) were added at 25C. The solution was stirred at 25 C for 16 h. After fractionation between 0.5 M HCl (50 mL) and EtOAc (150 mL), the aqueous layer was extracted with EtOAc (2 x 100mL). The combined organic fractions were washed with aqueous NaHCO3 (100 mL), H2O (2 x 100 mL) and brine (100 mL), dried (MgSO4), and concentrated under reduced pressure. The crude product was purified by column chromatography on silica (Buechi chromatography system, cyclohexane/ethyl acetate 99:1 to 96:4). Yield: 2.94 g (5.9 mmol, 61%) of a colorless solid.
(4R,6aR,9S,11bS)-prop-2-yn-1-yl-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
97%
With potassium carbonate; In toluene; acetonitrile; for 3h;Reflux;
(4R,6aR,9S,11bS)-prop-2-yn-1-yl-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate (10). <strong>[27975-19-5]Isosteviol</strong> (955 mg, 3 mmol), K2CO3 (829 mg, 6 mmol), and 3-bromoprop-1-yne (580 mg as 80% solution in toluene, 3.9 mmol) were dissolved in 60 mL acetonitrile. After reflux of the above mixture for 3 h, the resulting mixture was cooled to room temperature. The precipitate was then recovered through filtration and washed repeatedly with EtOAc. Combined mother liquids were concentrated under vacuum. Resulting residue was dissolved in EtOAc, washed with 1 N HCl and one more time with water (20 mL). The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude solid product was recrystallized from MeOH to yield 1036 mg (2.91 mmol, 97%) of white crystals of <strong>[27975-19-5]isosteviol</strong> propargyl ester (10). White solid (97%). 1H-NMR (CDCl3, 300 MHz, ppm): delta 4.73-4.57 (m, 2H), 2.64 (dd, J = 18.6, 3.8 Hz, 1H),2.45-2.41 (m, 1H), 2.19 (d, J = 13.2 Hz, 1H), 1.94-1.22 (m, 13H), 1.21 (s, 3H), 1.20-1.10 (m, 3H),1.05 (dd, J = 13.4, 4.1 Hz, 1H), 0.97 (s, 3H), 0.96-0.84 (m, 1H), 0.73 (s, 3H). 13C-NMR (CDCl3, 75MHz, ppm): delta 222.7, 176.5, 77.2, 74.7, 57.2, 54.8, 54.4, 51.6, 48.9, 48.6, 44.1, 41.6, 39.9, 39.6, 38.2,38.1, 37.5, 28.9, 21.8, 20.5, 20.0, 19.0, 13.7. HRMS: calcd. for C23H33O3 [M+H]+ 357.2424, found 357.2423. MP 115-116 C.
20 g of <strong>[58543-16-1]rebaudioside A</strong> were dissolved in 100 mL of 1N HCl and heated at 80 C over 3 h. The reaction mixture was submitted to liquid-liquid partition with EtOAc (5×200 mL) to yield 6.3 g of EtOAc extractable (hydrolysis reaction 1).
2-(4-methylpiperazin-1-yl)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
87%
With potassium carbonate; In acetonitrile; at 80℃; for 4h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and chlorinatedderivatives (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 4 h. After confirming the reactionprogress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixture was dissolvedwith 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then purified usingsilica gel column chromatography and eluted with petroleum ether:ethyl acetate (5:1) to obtain thetarget compound 2a-2e.
2-(4-ethylpiperazin-1-yl)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
84%
With potassium carbonate; In acetonitrile; at 80℃; for 4h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and chlorinatedderivatives (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 4 h. After confirming the reactionprogress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixture was dissolvedwith 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then purified usingsilica gel column chromatography and eluted with petroleum ether:ethyl acetate (5:1) to obtain thetarget compound 2a-2e.
2-oxo-2-(4-phenylpiperazin-1-yl)ethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
With potassium carbonate; In acetonitrile; at 80℃; for 4h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and chlorinatedderivatives (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 4 h. After confirming the reactionprogress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixture was dissolvedwith 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then purified usingsilica gel column chromatography and eluted with petroleum ether:ethyl acetate (5:1) to obtain thetarget compound 2a-2e.
2-(4-benzylpiperazin-1-yl)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83%
With potassium carbonate; In acetonitrile; at 80℃; for 4h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and chlorinatedderivatives (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 4 h. After confirming the reactionprogress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixture was dissolvedwith 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then purified usingsilica gel column chromatography and eluted with petroleum ether:ethyl acetate (5:1) to obtain thetarget compound 2a-2e.
2-(azepan-1-yl)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83%
With potassium carbonate; In acetonitrile; at 80℃; for 4h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and chlorinatedderivatives (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 4 h. After confirming the reactionprogress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixture was dissolvedwith 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then purified usingsilica gel column chromatography and eluted with petroleum ether:ethyl acetate (5:1) to obtain thetarget compound 2a-2e.
methyl (S)-2-phenyl-2-((4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxamido)acetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
70%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In chloroform; at 60℃; for 8h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), EDCHCl (42.2 mg, 0.22 mmol), HOBt (29.7 mg,0.22 mmol), Et3N (102 L, 0.30 mmol) and various amino acid esters (0.30 mmol) in CHCl3 (10 mL)was stirred at 60 C for 8 h. After confirming the reaction progress by thin-layer chromatography, thesolvent was evaporated in vacuo, the mixture was dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then purified using silica gel column chromatography andeluted with a gradient of petroleum ether:ethyl acetate (10:1-5:1) to obtain the target compound3a-3d.
methyl ((4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carbonyl)-D-phenylalaninate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
76%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In chloroform; at 60℃; for 8h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), EDCHCl (42.2 mg, 0.22 mmol), HOBt (29.7 mg,0.22 mmol), Et3N (102 L, 0.30 mmol) and various amino acid esters (0.30 mmol) in CHCl3 (10 mL)was stirred at 60 C for 8 h. After confirming the reaction progress by thin-layer chromatography, thesolvent was evaporated in vacuo, the mixture was dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then purified using silica gel column chromatography andeluted with a gradient of petroleum ether:ethyl acetate (10:1-5:1) to obtain the target compound3a-3d.
methyl ((4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carbonyl)-L-valinate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
71%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In chloroform; at 60℃; for 8h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), EDCHCl (42.2 mg, 0.22 mmol), HOBt (29.7 mg,0.22 mmol), Et3N (102 L, 0.30 mmol) and various amino acid esters (0.30 mmol) in CHCl3 (10 mL)was stirred at 60 C for 8 h. After confirming the reaction progress by thin-layer chromatography, thesolvent was evaporated in vacuo, the mixture was dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then purified using silica gel column chromatography andeluted with a gradient of petroleum ether:ethyl acetate (10:1-5:1) to obtain the target compound3a-3d.
methyl ((4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carbonyl)-L-tryptophanate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
74%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In chloroform; at 60℃; for 8h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), EDCHCl (42.2 mg, 0.22 mmol), HOBt (29.7 mg,0.22 mmol), Et3N (102 L, 0.30 mmol) and various amino acid esters (0.30 mmol) in CHCl3 (10 mL)was stirred at 60 C for 8 h. After confirming the reaction progress by thin-layer chromatography, thesolvent was evaporated in vacuo, the mixture was dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then purified using silica gel column chromatography andeluted with a gradient of petroleum ether:ethyl acetate (10:1-5:1) to obtain the target compound3a-3d.
2-oxo-2-(phenylamino)ethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
86%
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentchloroacetanilides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. After confirmingthe reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixturewas dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then puried using silica gel column chromatography and eluted with a gradient of petroleum ether:ethylacetate (4:1-5:1) to obtain the target compound4a-4j.
2-((2-chlorophenyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83%
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentchloroacetanilides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. After confirmingthe reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixturewas dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then puried using silica gel column chromatography and eluted with a gradient of petroleum ether:ethylacetate (4:1-5:1) to obtain the target compound4a-4j.
2-((3-chlorophenyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentchloroacetanilides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. After confirmingthe reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixturewas dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then puried using silica gel column chromatography and eluted with a gradient of petroleum ether:ethylacetate (4:1-5:1) to obtain the target compound4a-4j.
2-((4-chlorophenyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
84%
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentchloroacetanilides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. After confirmingthe reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixturewas dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then puried using silica gel column chromatography and eluted with a gradient of petroleum ether:ethylacetate (4:1-5:1) to obtain the target compound4a-4j.
2-((2-fluorophenyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentchloroacetanilides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. After confirmingthe reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixturewas dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then puried using silica gel column chromatography and eluted with a gradient of petroleum ether:ethylacetate (4:1-5:1) to obtain the target compound4a-4j.
2-((3-fluorophenyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentchloroacetanilides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. After confirmingthe reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixturewas dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then puried using silica gel column chromatography and eluted with a gradient of petroleum ether:ethylacetate (4:1-5:1) to obtain the target compound4a-4j.
2-((4-fluorophenyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
90%
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
General procedure: A mixture of isosteviol (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentchloroacetanilides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. After confirmingthe reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixturewas dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then puried using silica gel column chromatography and eluted with a gradient of petroleum ether:ethylacetate (4:1-5:1) to obtain the target compound4a-4j.
2-((4-nitrophenyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
78%
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentchloroacetanilides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. After confirmingthe reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixturewas dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then puried using silica gel column chromatography and eluted with a gradient of petroleum ether:ethylacetate (4:1-5:1) to obtain the target compound4a-4j.
2-((4-methoxyphenyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentchloroacetanilides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. After confirmingthe reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixturewas dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then puried using silica gel column chromatography and eluted with a gradient of petroleum ether:ethylacetate (4:1-5:1) to obtain the target compound4a-4j.
2-((2,5-dimethoxyphenyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
79%
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentchloroacetanilides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. After confirmingthe reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixturewas dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then puried using silica gel column chromatography and eluted with a gradient of petroleum ether:ethylacetate (4:1-5:1) to obtain the target compound4a-4j.
2-oxo-2-(((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)amino)ethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and different phenyl1,2,3-triazole chloroacetamides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. Afterconfirming the reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo,the mixture was dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). Themixture was then purified using silica gel column chromatography and eluted with petroleumether:ethyl acetate (1:1) to obtain the target compound 5a-5e.
2-(((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
82%
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and different phenyl1,2,3-triazole chloroacetamides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. Afterconfirming the reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo,the mixture was dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). Themixture was then purified using silica gel column chromatography and eluted with petroleumether:ethyl acetate (1:1) to obtain the target compound 5a-5e.
2-(((1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83%
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and different phenyl1,2,3-triazole chloroacetamides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. Afterconfirming the reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo,the mixture was dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). Themixture was then purified using silica gel column chromatography and eluted with petroleumether:ethyl acetate (1:1) to obtain the target compound 5a-5e.
2-oxo-2-(((1-(p-tolyl)-1H-1,2,3-triazol-4-yl)methyl)amino)ethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83%
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and different phenyl1,2,3-triazole chloroacetamides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. Afterconfirming the reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo,the mixture was dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). Themixture was then purified using silica gel column chromatography and eluted with petroleumether:ethyl acetate (1:1) to obtain the target compound 5a-5e.
2-(((1-(3,4-dichlorophenyl)-1H-1,2,3-triazol-4-yl)methyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
79%
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and different phenyl1,2,3-triazole chloroacetamides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. Afterconfirming the reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo,the mixture was dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). Themixture was then purified using silica gel column chromatography and eluted with petroleumether:ethyl acetate (1:1) to obtain the target compound 5a-5e.
2-(((diethoxyphosphoryl)(phenyl)methyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
With potassium carbonate; In acetonitrile; at 80℃; for 3h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentphosphonic acid [[(chloroacetyl) amino] phenylmethyl]-diethyl esters (0.21 mmol) in CH3CN (10mL) was stirred at 80 C for 3 h. After confirming the reaction progress by thin-layer chromatography,the solvent was evaporated in vacuo, the mixture was dissolved with 15 mL ethyl acetate and thenwashed with saline (5 mL x 3). The mixture was then purified using silica gel column chromatographyand eluted with a gradient of petroleum ether:ethyl acetate (3:1-1:1) to obtain the target compound6a-6e.
2-(((4-chlorophenyl)(diethoxyphosphoryl)methyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11btrimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83%
With potassium carbonate; In acetonitrile; at 80℃; for 3h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentphosphonic acid [[(chloroacetyl) amino] phenylmethyl]-diethyl esters (0.21 mmol) in CH3CN (10mL) was stirred at 80 C for 3 h. After confirming the reaction progress by thin-layer chromatography,the solvent was evaporated in vacuo, the mixture was dissolved with 15 mL ethyl acetate and thenwashed with saline (5 mL x 3). The mixture was then purified using silica gel column chromatographyand eluted with a gradient of petroleum ether:ethyl acetate (3:1-1:1) to obtain the target compound6a-6e.
2-(((diethoxyphosphoryl)(4-methoxyphenyl)methyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11btrimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
With potassium carbonate; In acetonitrile; at 80℃; for 3h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentphosphonic acid [[(chloroacetyl) amino] phenylmethyl]-diethyl esters (0.21 mmol) in CH3CN (10mL) was stirred at 80 C for 3 h. After confirming the reaction progress by thin-layer chromatography,the solvent was evaporated in vacuo, the mixture was dissolved with 15 mL ethyl acetate and thenwashed with saline (5 mL x 3). The mixture was then purified using silica gel column chromatographyand eluted with a gradient of petroleum ether:ethyl acetate (3:1-1:1) to obtain the target compound6a-6e.
2-(((diethoxyphosphoryl)(p-tolyl)methyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
84%
With potassium carbonate; In acetonitrile; at 80℃; for 3h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentphosphonic acid [[(chloroacetyl) amino] phenylmethyl]-diethyl esters (0.21 mmol) in CH3CN (10mL) was stirred at 80 C for 3 h. After confirming the reaction progress by thin-layer chromatography,the solvent was evaporated in vacuo, the mixture was dissolved with 15 mL ethyl acetate and thenwashed with saline (5 mL x 3). The mixture was then purified using silica gel column chromatographyand eluted with a gradient of petroleum ether:ethyl acetate (3:1-1:1) to obtain the target compound6a-6e.
2-(((3,4-dichlorophenyl)(diethoxyphosphoryl)methyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
With potassium carbonate; In acetonitrile; at 80℃; for 3h;
General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentphosphonic acid [[(chloroacetyl) amino] phenylmethyl]-diethyl esters (0.21 mmol) in CH3CN (10mL) was stirred at 80 C for 3 h. After confirming the reaction progress by thin-layer chromatography,the solvent was evaporated in vacuo, the mixture was dissolved with 15 mL ethyl acetate and thenwashed with saline (5 mL x 3). The mixture was then purified using silica gel column chromatographyand eluted with a gradient of petroleum ether:ethyl acetate (3:1-1:1) to obtain the target compound6a-6e.
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