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CAS No. : | 19420-57-6 | MDL No. : | MFCD00050427 |
Formula : | C26H54NO7P | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IHNKQIMGVNPMTC-RUZDIDTESA-N |
M.W : | 523.68 | Pubchem ID : | 497299 |
Synonyms : |
|
Chemical Name : | (R)-2-Hydroxy-3-(stearoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With tris hydrochloride; sodium docusate; calcium chloride; In 2,2,4-trimethylpentane; at 40℃; for 0.5h;pH 8.5;Enzymatic reaction; | General procedure: Hydrolysis of 1,2-diacyl-sn-glycero-3-phosphocholines 2a-e was carried out according to the method described by Morgado et al.[30] Two solutions, A: 0.635 mmol of 2a-e in 13.2 mL isooctane, and B: 174 mg (0.393 mmol) of sodium docusate (AOT) in 13.2mL isooctane, were pre-incubated for 0.5 h at 40 C on a magnetic stirrer. Then, 262 mL of PLA2 (10000 U mL-1; 1 U is equivalent to the amount of enzyme producing 1 mmole of free fatty acid per minute at pH 8 and 40 C) and the same volume of Tris-HCl buffer (0.1 M, pH 8.5) with 0.75M of CaCl2 were then added to solution B and the reaction was started by adding solution A. The progress of the enzymatic reactions was monitored by TLC (65 : 25 : 4 CHCl3/CH3OH/H2O v/v/v). The reaction was carried out for 30 min. The enzyme was separated from the reaction mixture using diatomaceous earth (Celite 545) and the solvent was evaporated to dryness at 40 Cunder vacuum. 1-Acyl LPCs 3a-e were purified on a silica gelcolumn (65 : 25 : 4 CHCl3/CH3OH/H2O v/v/v). Product containing fractions of Rf 0.3 were collected and solvent evaporated under vacuum (45 C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 2: Stearoyl-lyso-PC A suspension of 0.5 g of GPC, 0.5 g of DBTO (1 eq), and 10 ml of methanol was stirred at reflux until a clear solution was obtained (1 hr); the solvent was evaporated from the solution to give a residual volume of 1 ml. 5 ml of IPA was added, the mixture was concentrated again at ordinary pressure to give a residual volume of 1 ml, and 5 ml of IPA was added. 0.324 ml of TEA (1.2 eq) and 0.62 g of palmitoyl chloride (1.2 eq) were dropped in at 25C. At the end of the dropping, the conversion (31P-NMR) was 92%, and the ratio between the two forms of lyso-PC was 1:9 in favour of the compound acylated at position sn-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 48h;Inert atmosphere; Darkness; | General procedure: Compounds 4c-e were prepared from 1-stearoyl-2-hydroxysn-glycero-3-phosphocholine (3a) (100 mg, 0.191 mmol) by adding 106 mg (0.381 mmol) of a mixture of CLA isomers (1c), cis-9,trans-11 (1d) or trans-10,cis-12 CLA (1e) dissolved in 5.7mL of anhydrous CH2Cl2, DMAP (53.8 mg, 0.191 mmol), and finally a solution of DCC (119 mg, 0.419 mmol) in 1.9 mL of CH2Cl2. The reaction was carried out for 48 h under a nitrogen atmosphere in the dark and at ambient temperature. The precipitate that was formed in the reaction mixture was removed using a Shott funnel. Ion-exchange resin (Dowex 50W X8, Hform) was added to the filtrate and the mixture was stirred for 30 min to dislodge DMAP. The Dowex resin was filtered off and the solvent was evaporated under vacuum. The crude PC was purified on a silica gel column (65 : 25 : 4 CHCl3/CH3OH/H2O v/v/v). Product-containing fractions of Rf 0.4 were collected and solvent evaporated under vacuum (45 C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 48h;Inert atmosphere; Darkness; | General procedure: Compounds 4c-e were prepared from 1-stearoyl-2-hydroxysn-glycero-3-phosphocholine (3a) (100 mg, 0.191 mmol) by adding 106 mg (0.381 mmol) of a mixture of CLA isomers (1c), cis-9,trans-11 (1d) or trans-10,cis-12 CLA (1e) dissolved in 5.7mL of anhydrous CH2Cl2, DMAP (53.8 mg, 0.191 mmol), and finally a solution of DCC (119 mg, 0.419 mmol) in 1.9 mL of CH2Cl2. The reaction was carried out for 48 h under a nitrogen atmosphere in the dark and at ambient temperature. The precipitate that was formed in the reaction mixture was removed using a Shott funnel. Ion-exchange resin (Dowex 50W X8, Hform) was added to the filtrate and the mixture was stirred for 30 min to dislodge DMAP. The Dowex resin was filtered off and the solvent was evaporated under vacuum. The crude PC was purified on a silica gel column (65 : 25 : 4 CHCl3/CH3OH/H2O v/v/v). Product-containing fractions of Rf 0.4 were collected and solvent evaporated under vacuum (45 C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73.8% | 5 ml of reaction flask was added 190 g of C18-<strong>[19420-57-6]lysophosphatidylcholine</strong>, 9.5 g of 4-dimethylaminopyridine (DMAP) and 260 g of valproic acid anhydride to 60 C for 4 h. The solution was clarified and cooled to 20 C The volume of acetone, dropping, cooled to 0 C for 2 h, suction, vacuum drying at 50 C, the resulting crude product in the 5L reaction flask by adding 1.1 times the volume of anhydrous ethanol 20 C stirring dissolved, dropping 12.5 times the volume of acetone , The residue was cooled to 0 C for 2 h, filtered, and vacuum dried at 50 C to obtain 174 g of C18-DP-VPA in a yield of 73.8% and a purity of 99.2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.3% | (1) Preparation of choline glycerophosphate dibutyltin oxide complex: 30 g (0.1 lmol) of choline glycerophosphate was dissolved in 500 ml of absolute ethanol, added with 24.9 g (0.1 mol) of dibutyltin oxide, heated to reflux for 0.5 hours, cooled to room temperature, filtered, wash the filter cake with anhydrous isopropanol to the filtrate without choline glycerophosphate, and dry the filter cake under vacuum at 60 C to obtain 50.6 g of white choline glycerophosphate dibutyltin oxide complex. (2) Under stirring, 25.3 g (0.05 mol) of glycerophosphocholine-dibutyltin oxide complex was placed in 3000 ml of tetrahydrofuran, 6 g (0.059 mol) of triethylamine, 16 g (0.053 mol) of stearic acid chloride , Stirred at 50 C for 3 hours, after the reaction was completed, cooled to room temperature, 200 ml of distilled water was added and stirred for 0.5 hours, filtered and the filtrate was concentrated under reduced pressure to give 25 g crude stearyl lysolecithin. [0016] The crude product of 25 g stearyl lysolecithin was recrystallized from a mixture of acetonitrile-ethanol in a volume ratio of 100: 1 to obtain 22.5 g of stearyl lysolecithin product with a yield of 83.3% and a purity of 98.1 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | 0.540 g (0.001 mol) of camptothecin-20-0-(3, 3’-dithiodipropionyl) monoester was dissolved into 200 ml of dichloromethane, add 0.5 g of 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride, 0.1 g of 4-dimethylaminopyridine, at room temperature, after stirring for 3 hours add 0.523 g (0.001 mol) of 1-stearoyl-Sn-glycerol-3-phosphocholine, at room temperature, after stirring for 72 hours, the reaction solution was poured into 500 ml of ice water, filtered, at 50 C, vacuum drying the filter cake, the filter cake was subjected to silica gel column chromatography (methanol: chloroform: water = 25:65:2), obtained yellow 1-stearoyl-2-(camptothecin-20-0-(3, 3dithiodipropionyl) monoester) glycerol-3-phosphocholine 0.21 g (i.e. phospholipids analogue), yield 20%. | |
20% | 0.540 g (0.001 mol) of camptothecin-20-O-(3,3'-dithiodipropionyl)monoester was dissolved in 50 ml of dimethyl sulfoxide, and 0.5 g of 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, 0.1 g of 4-dimethylaminopyridine, stirred at room temperature for 3 hours, then added 0.523 g (0.001 mol) of 1-stearoyl-sn-glycerol-3-phosphocholine, room temperature after stirring for 72 hours, the reaction liquid was poured into 500 ml of ice water, filtered, and the filter cake was dried under vacuum at 50 C, and the filter cake was subjected to silica gel column chromatography (methanol: chloroform: water = 25:65:2). yellow 1-stearoyl-2-(camptothecin-20-O-(3,3'-dithiodipropionyl) monoester)glycerol-3-phosphocholine 0.21 g (ie lecithin analog) in 20% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; at 20℃; for 72h; | (4) 500 mg (1.04 mM) of the compound 3 prepared in the step (3) was dissolved in 20 ml of alcohol-free chloroform, and then 400 mg (2.08 mM) of EDC.HCL was added, respectively. 254mg (2.08mM) DMAP, 281 mg (2.08 mM) of HOBT and 545 mg (1.04 mM) of lyso-PC, After reacting at room temperature for 72 h, After the reaction, the product is separated and purified by thin layer chromatography. Use a thick preparation plate (20*20cm, coating thickness 0.4-0.5mm), The developing agent is a mixed solution of dichloromethane and methanol, The ratio of dichloromethane to methanol was 10:1, and an off-white solid was obtained. That is, the compound 4 is fluorinated fluorescent phospholipid, and the yield is about 32%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With dmap; dicyclohexyl-carbodiimide; In chloroform; at 20℃; for 120h; | Intermediate 2 (300 mg, 0.57 mmol) was dissolved in CHCh (10 mL), then fatty acid (1.15 mmol), 4-DMAP (140 mg, 1.15 mmol) and DCC (236 mg, 1.15 mmol) were added. The reaction mixture was stirred at 20 C for 5 days, the solids were filtered and washed with CHCh. The solvent was evaporated and the residue was chromatographed on silica in CHCh, CHCh- MeOH (2: 1, 1 : 1, 1 :2) and MeOH. The pure fractions were evaporated to give product as a colorless waxy substance. Rf 0.40 (CHCh, MeOH, cone. M 13 :5: 1). (0237) [0160] l-Acyl-2-linoleyl-sn-glycero-3-phosphatidylcholine (3a). Yield 344 mg (77%). NMR (CDCh) d 5.36 (m, 4H), 4.41 (m, 1H), 4.30 (m, 2H), 4.11 (dd, J= 12.1, 7.4 Hz, (0238) 1H), 4.00-3.85 (m, 2H), 3,76 (m, 2H), 3.33 (m, 9H), 2.80 (m, 2H), 2.28 (m, 4H), 2.10 (m, 4H), 1.58 (m, 4H), 1.24 (m, 40H), 0.97 (m, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With 1-methyl-1H-imidazole; 2-methyl-6-nitrobenzoic anhydride; In dichloromethane; at 20℃; for 16h; | To a solution of alpha-linolenic acid (1h) (55 mg, 0.198 mmol) in CH2Cl2 (2 mL) were added NMI (0.036 mL, 0.456 mmol) and MNBA (158 mg, 0.459 mmol). After 20 min of stirring at rt, lyso-PC 2a (53 mg, 0.101 mmol) was added. The mixture was stirred at rt for 16 h and concentrated to give a residue, which was purified by chromatography on silica gel (CHCl3/MeOH/H2O = 65:25:1 to 65:25:3) to afford PC 3h (61 mg, 77%): Rf = 0.08(CHCl3/MeOH/H2O = 65:25:1); 1H NMR (400 MHz, CD3OD) delta 0.90 (t, J = 7.2 Hz, 3 H),0.97 (t, J = 7.2 Hz, 3 H), 1.21-1.43 (m), 1.54-1.68 (m, 4 H), 2.02-2.14 (m, 4 H), 2.31 (t, J =7.6 Hz, 2 H), 2.34 (t, J = 7.6 Hz, 2 H), 2.81 (t, J = 6.0 Hz, 4 H), 3.22 (s, 9 H), 3.61-3.68 (m,2 H), 4.00 (t, J = 6.2 Hz, 2 H), 4.17 (dd, J = 12.1, 6.8 Hz, 1 H), 4.23-4.32 (m, 2 H), 4.44 (dd,J = 12.1, 3.0 Hz, 1 H), 5.20-5.27 (m, 1 H), 5.27-5.44 (m, 6 H); 13C NMR (100 MHz, CD3OD)delta 13.2, 13.4, 20.2, 22.4, 24.7, 25.1, 25.2, 26.9, 28.8, 28.90, 28.94, 29.0, 29.2, 29.35, 29.42,29.5, 31.7, 33.6, 33.7, 53.3 (t, J = 3.4 Hz, 3 C), 59.1 (d, J = 4.6 Hz), 62.2, 63.5 (d, J = 4.6Hz), 66.0 (m), 70.4 (d, J = 8.4 Hz), 126.9, 127.5, 127.8, 127.9, 129.7, 131.4, 173.0, 173.4;HRMS (FAB) calcd for C44H83O8NP [(M+H)+] 784.5856, found 784.5893. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With 1-methyl-1H-imidazole; 2-methyl-6-nitrobenzoic anhydride; In dichloromethane; at 20℃; for 24h;Inert atmosphere; | To a solution of acid 1a (48 mg, 0.192 mmol) in CH2Cl2 (1 mL)were added NMI (0.034 mL, 0.43 mmol) and MNBA (148 mg,0.430 mmol). After 20 min of stirring at rt, lyso-PC 2a (50 mg,0.0955 mmol) was added. The mixture was stirred at rt for 24 hunder nitrogen and concentrated to give a residue, which waspurified by chromatography on silica gel (CHCl3/MeOH/H2O =65:25:1 to 65:25:3) to afford PC 3a (63 mg, 87%): Rf = 0.21(CHCl3/MeOH/H2O = 65:25:3). 1H NMR (400 MHz, CD3OD): =0.89 (t, J = 6.8 Hz, 3 H), 1.27 (br s), 1.53-1.88 (m, 6 H), 2.30 (t, J =7.4 Hz, 2 H), 2.43-2.52 (m, 2 H), 2.72-2.83 (m, 2 H), 3.01 (dt, J =7.2, 4.2 Hz, 1 H), 3.10-3.16 (m, 1 H), 3.21 (s, 9 H), 3.60-3.66 (m,2 H), 3.76 (s, 9 H), 4.02 (t, J = 6.2 Hz, 2 H), 4.18 (dd, J = 12.0, 6.4Hz, 1 H), 4.23-4.31 (m, 2 H), 4.44 (dd, J = 12.0, 2.8 Hz, 1 H),5.22-5.29 (m, 1 H), 6.86 (dd, J = 8.4 Hz, 2 H), 7.19 (d, J = 8.4 Hz, 2H). 13C NMR (100 MHz, CD3OD): = 13.1, 21.70, 21.73, 22.3,24.6, 26.9, 28.8, 29.0, 29.1, 29.2, 29.4, 31.7, 32.9, 33.19, 33.21,33.4, 53.3 (t, J = 3.8 Hz, 3 C), 54.2, 56.81 and 56.84, 57.50 and57.53, 59.1 (d, J = 5.3 Hz), 62.2, 63.5 (d, J = 4.6 Hz), 66.0 (m), 70.6(d, J = 7.6 Hz), 113.6, 129.4, 129.8, 158.5, 172.8, 173.6. HRMS(FAB): m/z calcd for C40H71O10NP [M + H]+ 756.4816; found:756.4826. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With 1-methyl-1H-imidazole; 2-methyl-6-nitrobenzoic anhydride; In dichloromethane; at 20℃; for 18h; | To a solution of acid 1b (62 mg, 0.145 mmol) in CH2Cl2 (1.5 mL) were added NMI (0.026mL, 0.33 mmol) and MNBA (115 mg, 0.334 mmol). After 20 min of stirring at rt, lyso-PC2a (38 mg, 0.073 mmol) was added. The mixture was stirred at rt for 18 h and concentratedto give a residue, which was purified by chromatography on silica gel (CHCl3/MeOH/H2O =65:25:1 to 65:25:3) to afford 3b (50 mg, 74%): Rf = 0.25 (CHCl3/MeOH/H2O = 65:25:3); 1HNMR (400 MHz, CD3OD) δ 0.081, 0.084, 0.088, and 0.092 (4 s, total 6 H), 0.87-0.94 (m, 15H), 1.26-1.78 (m), 2.31 (t, J = 7.4 Hz, 2 H), 2.35 (t, J = 7.4 Hz, 2 H), 2.88-2.98 (m, 1 H),3.02-3.10 (m, 1 H), 3.23 (s, 9 H), 3.61-3.68 (m, 2 H), 3.85-3.94 (m, 1 H), 4.00 (t, J = 6.2Hz, 2 H), 4.17 (dd, J = 12.0, 6.8 Hz, 1 H), 4.23-4.32 (m, 2 H), 4.44 (dd, J = 12.0, 3.2 Hz, 1H), 5.21-5.28 (m, 1 H); 13C NMR (100 MHz, CD3OD) δ -5.6, -5.5, 13.2, 17.6, 22.3, 22.4,24.62, 24.64, 25.06, 25.10, 25.2, 26.3, 27.7, 27.8, 28.7, 28.9, 29.0, 29.13, 29.15, 29.2, 29.3,29.4, 29.5, 31.67, 31.74, 33.5, 33.7, 34.98, 35.04, 37.0, 37.6, 53.3 (t, J = 3.4 Hz, 3 C), 53.8and 54.4, 56.2 and 57.1, 59.1 (d, J = 4.5 Hz), 62.3, 63.5 (d, J = 5.3 Hz), 66.0 (m), 70.3, 70.4(d, J = 9.9 Hz), 173.0, 173.4; HRMS (FAB) calcd for C50H101O10NPSi [(M+H)+] 934.6932, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 1-methyl-1H-imidazole; 2-methyl-6-nitrobenzoic anhydride; In dichloromethane; at 20℃; for 19h; | To a solution of acid 1d (84 mg, 0.204 mmol) in CH2Cl2 (2 mL) were added NMI (0.036 mL,0.452 mmol) and MNBA (159 mg, 0.462 mmol). After 20 min of stirring at rt, lyso-PC 2a (50 mg, 0.0955 mmol) was added. The mixture was stirred at rt for 19 h and concentrated togive a residue, which was purified by chromatography on silica gel (CHCl3/MeOH/H2O =65:25:1 to 65:25:3) to afford 3d (70 mg, 80%): Rf = 0.30 (CHCl3/MeOH/H2O = 65:25:3); 1HNMR (400 MHz, CD3OD) δ 0.06 (s, 3 H), 0.07 (s, 3 H), 0.87-0.94 (m, 15 H), 1.24-1.48 (m),1.54-1.66 (m, 4 H), 1.99-2.10 (m, 2 H), 2.12-2.26 (m, 2 H), 2.31 (t, J = 7.4 Hz, 2 H), 2.34(t, J = 7.2 Hz, 2 H), 3.22 (s, 9 H), 3.61-3.66 (m, 2 H), 3.66-3.74 (m, 1 H), 4.00 (t, J = 6.0Hz, 2 H), 4.17 (dd, J = 12.1, 7.0 Hz, 1 H), 4.23-4.32 (m, 2 H), 4.44 (dd, J = 12.1, 2.8 Hz, 1H), 5.20-5.28 (m, 1 H), 5.35-5.48 (m, 2 H); 13C NMR (100 MHz, CD3OD) δ -5.5, -5.3, 13.2,17.6, 22.37, 22.43, 24.67, 24.69, 25.15, 25.17, 27.2, 28.86, 28.93, 29.0, 29.1, 29.2, 29.3, 29.4,29.48, 29.53, 31.74, 31.77, 33.6, 33.7, 35.0, 36.6, 53.3 (t, J = 3.8 Hz, 3 C), 59.1 (d, J = 5.4Hz), 62.3, 63.5 (d, J = 5.3 Hz), 66.0 (m), 70.4 (d, J = 7.6 Hz), 72.3, 125.7, 131.0, 173.0,173.3; HRMS (FAB) calcd for C50H101O9NPSi [(M+H)+] 918.6983, found 918.6964. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With 1-methyl-1H-imidazole; 2-methyl-6-nitrobenzoic anhydride; In dichloromethane; at 20℃; for 30h; | To a solution of acid 1f (29 mg, 0.067 mmol) in CH2Cl2 (1 mL) were added NMI (0.024 mL,0.30 mmol) and MNBA (102 mg, 0.296 mmol). After 20 min of stirring at rt, lyso-PC 2a (17mg, 0.0319 mmol) was added. The mixture was stirred at rt for 30 h and concentrated to afford a residue, which was purified by chromatography on silica gel (CHCl3/MeOH/H2O =65:25:1 to 65:25:3) to afford 3f (28 mg, 90%): Rf = 0.23 (CHCl3/MeOH/H2O = 65:25:3); 1HNMR (400 MHz, CD3OD) δ 0.04 (s, 3 H), 0.07 (s, 3 H), 0.89 (t, J = 7.2 Hz, 3 H), 0.90 (t, J= 7.2 Hz, 3 H), 0.92 (s, 9 H), 1.12 (br s), 1.48-1.74 (m, 6 H), 2.09-2.17 (m, 2 H), 2.31 (t, J= 7.4 Hz, 2 H), 2.38 (t, J = 7.4 Hz, 2 H), 2.83 (t, J = 5.8 Hz, 2 H), 2.86 (t, J = 5.8 Hz, 2 H),2.93-3.00 (m, 2 H), 3.22 (s, 9 H), 3.61-3.68 (m, 2 H), 3.94-4.06 (m, 2 H), 4.13-4.22 (m, 2H), 4.23-4.33 (m, 2 H), 4.44 (dd, J = 12.0, 2.8 Hz, 1 H), 5.21-5.28 (m, 1 H), 5.32-5.43 (m,7 H), 5.64 (dd, J = 15.1, 6.2 Hz, 1 H), 5.99 (t, J = 11.1 Hz, 1 H), 6.53 (dd, J = 15.1, 11.1 Hz,1 H); 13C NMR (100 MHz, CD3OD) δ -5.9, -5.4, 8.7, 13.1, 17.7, 22.4, 24.5, 24.6, 25.1, 25.2,25.6, 26.1, 28.8, 29.09, 29.12, 29.3, 29.4, 30.8, 31.7, 33.1, 33.5, 53.3 (t, J = 3.5 Hz, 3 C),59.1 (d, J = 3.8 Hz), 62.2, 63.5 (d, J = 3.0 Hz), 66.0 (m), 70.4 (d, J = 6.8 Hz), 74.2, 124.3,127.5, 127.7, 127.9, 128.0, 128.57, 128.59, 128.7, 136.7, 172.9, 173.4; HRMS (FAB) calcdfor C52H96O9NPSiNa [(M+Na)+] 960.6490, found 960.6475. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With 1-methyl-1H-imidazole; 2-methyl-6-nitrobenzoic anhydride; In dichloromethane; at 20℃; for 20h; | To a solution of acid 1j (24 mg, 0.113 mmol) in CH2Cl2 (1 mL) were added NMI (0.020 mL,0.25 mmol) and MNBA (88 mg, 0.256 mmol). After 20 min of stirring at rt, lyso-PC 2a (30mg, 0.057 mmol) was added. The mixture was stirred at rt for 20 h and concentrated to give a residue, which was purified by chromatography on silica gel (CHCl3/MeOH/H2O = 65:25:1to 65:25:3) to afford 3j (33 mg, 77%): Rf = 0.13 (CHCl3/MeOH/H2O = 65:25:3); 1H NMR (400 MHz, CD3OD) δ 0.90 (t, J = 6.8 Hz, 3 H), 1.27 (br s), 1.53-1.67 (m, 2 H), 1.88 (quint.,J = 7.2 Hz, 2 H), 2.34 (t, J = 7.2 Hz, 2 H), 2.47 (t, J = 7.0 Hz, 2 H), 2.51 (t, J = 7.2 Hz, 2 H),3.22 (s, 9 H), 3.61-3.67 (m, 2 H), 3.97-4.07 (m, 2 H), 4.20 (dd, J = 12.0, 6.8 Hz, 1 H), 4.23-4.32 (m, 2 H), 4.45 (dd, J = 12.0, 3.4 Hz, 1 H), 5.22-5.30 (m, 1 H), 7.30-7.40 (m, 3 H), 7.43-7.49 (m, 2 H); 13C NMR (100 MHz, CD3OD) δ 14.5, 19.5, 23.8, 24.7, 26.0, 30.2, 3047, 30.50,30.7, 30.8, 33.1, 33.8, 34.9, 54.7 (t, J = 3.4 Hz, 3 C), 60.5 (d, J = 4.6 Hz), 63.5, 64.9 (d, J =5.4 Hz), 66.6, 67.5 (m), 72.1 (d, J = 7.6 Hz), 75.0, 75.8, 84.2, 123.2, 129.6, 130.2, 133.5,173.8, 175.0; HRMS (FAB) calcd for C40H65O8NP [(M+H)+] 718.4448, found 718.4443. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With 1-methyl-1H-imidazole; 2-methyl-6-nitrobenzoic anhydride; In dichloromethane; at 20℃; for 22h; | To a solution of eicosapentaenoic acid (1i) (35 mg, 0.116 mmol) in CH2Cl2 (1 mL) were added NMI (0.021 mL, 0.26 mmol) and MNBA (95 mg, 0.276 mmol). After 20 min of stirring at rt, lyso-PC 2a (29 mg, 0.0554 mmol) was added. The mixture was stirred at rt for 22 h and concentrated to afford a residue, which was purified by chromatography on silica gel (CHCl3/MeOH/H2O = 65:25:1 to 65:25:3) to afford 3i (41 mg, 92%): Rf = 0.17(CHCl3/MeOH/H2O = 65:25:3); 1H NMR (400 MHz, CD3OD) δ 0.90 (t, J = 6.8 Hz, 3 H),0.97 (t, J = 7.6 Hz, 3 H), 1.28 (br s), 1.54-1.64 (m, 2 H), 1.64-1.76 (m, 2 H), 2.04-2.18 (m,4 H), 2.31 (t, J = 7.6 Hz, 2 H), 2.36 (t, J = 7.6 Hz, 2 H), 2.78-2.92 (m, 8 H), 3.23 (s, 9 H),3.61-3.68 (m, 2 H), 4.00 (t, J = 6.0 Hz, 2 H), 4.17 (dd, J = 12.1, 7.0 Hz, 1 H), 4.23-4.32 (m,2 H), 4.44 (dd, J = 12.1, 3.2 Hz, 1 H), 5.21-5.28 (m, 1 H), 5.28-5.44 (m, 10 H); 13C NMR(100 MHz, CD3OD) δ 13.2, 13.4, 20.2, 22.4, 24.5, 24.6, 25.1, 25.21, 25.22, 26.2, 28.9, 29.11,29.14, 29.3, 29.4, 29.5, 31.7, 33.1, 33.5, 53.3 (t, J = 3.8 Hz, 3 C), 59.1 (d, J = 4.6 Hz), 62.3,63.4 (d, J = 5.3 Hz), 66.0 (m), 70.4 (d, J = 8.4 Hz), 126.8, 127.5, 127.72, 127.78, 127.83,128.1, 128.58, 128.60, 131.4, 172.9, 173.4; HRMS (FAB) calcd for C46H83O8NP [(M+H)+]808.5856, found 808.5881. The structure of 3i was also supported by 13C-APT NMRspectrum (see page S33). |