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CAS No. : | 729596-46-7 |
Formula : | C20H18O7 |
M.W : | 370.35 |
SMILES Code : | O=C(O[C@@H]([C@]1(O)C)[C@@H](COC(C2=CC=CC=C2)=O)OC1=O)C3=CC=CC=C3 |
MDL No. : | MFCD21607994 |
* 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 |
---|---|---|
90.5% | With pyridine; at 20℃; for 5h;Cooling with ice; | 35 g of Compound 1 1, 61 g of protective reagent R1 and 200 mL of dichloromethane were added to the reaction flask, R1 was benzoyl chloride, and the mixture was cooled in an ice bath, stirred, and 35 g of pyridine was slowly added dropwise. The reaction was stirred at 15 ° C for 5 hours, washed with water, and then dried and crystallised to give Compound A1 in a yield of 90.2 percent. |
81% | With triethylamine; In ethyl acetate;Cooling with ice; | 2-C-methyl-D-ribono-gamma-lactone 5 (3.24 g, 20.0 mmoL) was suspended in 60 mL ethyl acetate, and benzoylchloride (6 mL, 40 mmoL, 2 eq) was added under ice bath. To this solution wasslowly added triethylamine (6.09 mL, 44 mmoL, 2.2 eq) in a period of at leastthree hours, and the reaction mixture continued to be stirred overnight. Theinsoluble substance was filtrated away, and washed with 20 mL ethyl acetate. The combined filtrate was washed withsaturated NaHCO3 solution (20 mL), 1 M HCl (20 mL × 2) and brine (20mL), then dried over Na2SO4 and evaporated. The residuewas slurryed with toluene to afford a white solid (6.0 g, 81percent). 1HNMR (400 MHz, CDCl3): delta8.09 (dd, 2H, J = 8.4, 1.2 Hz), 8.03(dd, 2H, J = 8.4, 1.2 Hz),7.62-7.77(m, 1H), 7.56-7.63(m, 1H), 7.49 (t, 2H, J = 8.0 Hz), 7.44 (t, 2H, J =8.0 Hz), 5.44 (d, 1H, J = 6.0 Hz),4.95-5.01(m, 1H), 4.75 (dd, 1H, J =12.4, 4.0 Hz), 4.63 (dd, 1H, J = 12.4,6.0 Hz), 1.69 (s, 3H). ESI-MS m/z: 371.2 [M + H]+. |
81% | With triethylamine; In ethyl acetate;Cooling with ice; | The 2-C-methyl-D- ribotide -1,4-lactone (3.24g, 20mmoL) suspended in 60 ml of ethyl acetate, under the condition of ice bath, dripping benzoyl chloride (4.6 ml, 40mmoL, 2eq). Is omitted, then slowly dripped into triethylamine (6.09 ml, 44mmoL, 2.2eq), at least 3 hours drop end, reaction sleepovers. Filtering, with 20 ml ethyl acetate wash the filter cake, combined with the phase, with saturated sodium bicarbonate, 1M dilute hydrochloric acid and saturated salt water washing, drying by anhydrous magnesium sulphate. Filtering, evaporating solvent under reduced pressure, toluene and petroleum ether beating to obtain 6g white solid, yield 81percent. |
70 - 72% | With triethylamine; In acetonitrile; at 20℃; for 3.5h; | 100 g (0.617 moles) of 2-C-methyl-D-ribopentono-1,4-lactone is added with stirring to 600 ml of acetonitrile, then 143 ml (1.23 moles) of benzoyl chloride is added in the suspension at room temperature. A mixture of 171 ml (1.23 moles) of triethylamine and 171 ml of acetonitrile is slowly (3 hours) dripped at room temperature. The reaction is stirred for 30 min. at room temperature, then an HPLC test is carried out. Thereafter 900 ml of water is added and oil is obtained. The oil is concentrated to syrup and the product crystallizes from hot toluene (490 ml). 160 g of 3,5-di-O-benzoyl-2-C-methyl-D-ribopentono-1,4-lactone is obtained as a white solid. Yield=70percent. Pf: 110 C.13.2 Kg of acetonitrile are introduced into a 100 l reactor while stirring. 2.8 Kg (17.3 moles) of 2-C-methyl-D-ribopentono-1,4-lactone and 4.76 Kg (33.8 moles) of benzoyl chloride are added. In another reactor a solution made up by diluting 3.43 Kg (33.9 moles) of triethylamine and 3.71 Kg of acetonitrile is prepared. This solution is dripped in the 100 l reactor during 3 hours keeping the temperature at 20° C.+/-2° C. After 30 min. from the end of the addition an HPLC test is carried out to estimate the amount of the starting material that is smaller than 1percent compared to 3,5-di-O-benzoyl-2-C-methyl-D-ribopentono-1,4-lactone and the amount of 2,3,5-tri-O-benzoyl-2-C-methyl-D-ribopentono-1,4-lactone is smaller than 10percent. Afterward 25 l of demineralised water is introduced into the reactor, the stirring is stopped and the layers are separated. After 5 min. stirring and 1 hour at rest, the layers are separated: the organic (weight 12.9 Kg) is transferred in a 25 l glass reactor and then washed with 10 l of demineralised water. The layers are separated: the organic phase is put away, and the aqueous phase is put together with the aqueous layer of the first extraction and they are washed with 1.5 l of toluene. The stirring water layer is eliminated, the organic layer is mixed to the organic phase of the first extraction. The organic layer is concentrated to syrup under vacuum at T<50° C. In another reactor 14.5 Kg of toluene is heated at 50° C. and then it is added to the syrup. The mixture is stirred 1 hour then it is cooled at 20° C. It is filtered and the panel is washed with 3 Kg of toluene and with 2.1 Kg of hexane. 4.6 Kg of 3,5-di-O-benzoyl-2-C-methyl-D-ribopentono-1,4-lactone is obtained. Yield=72percent. |
70 - 72% | With triethylamine; In ethyl acetate; at 20℃; for 3.5h; | 20 g (0.12 moles) of 2-C-methyl-D-ribopentono-1,4-lactone is added by stirring to 120 ml of ethyl acetate, then 27 ml (0.23 moles) of benzoyl chloride is added in the suspension at room temperature. A mixture of 32 ml (0.23 moles) of triethylamine and 32 ml of ethyl acetate is slowly (3 hours) dripped at room temperature cooling down to keep temperature lower then 20 C. The reaction is stirred for 30 min. at room temperature, and then an HPLC test is carried out. 180 ml of demineralised water is added, the organic phase is concentrated to a syrup and 3,5-di-O-benzoyl-2-C-methyl-D-ribopentono-1,4-lactone crystallizes from 130 ml of toluene preheated at 50 C. 32 g of 3,5-di-O-benzoyl-2-C-methyl-D-ribopentono-1,4-lactone is obtained. Yield=72percent.37.8 Kg of ethyl acetate is introduced in a 200 l reactor and then placed under stirring. 7 Kg (43.2 moles) of 2-C-methyl-D-ribopentono-1,4-lactone and 11.75 Kg (83.6 moles) of benzoyl chloride are added. In another reactor a solution obtained by diluting 8.5 Kg (83.6 moles) of triethylamine in 10.5 Kg of ethyl acetate is prepared. 200 l of this solution is added in the 200 1 reactor during 3 hours keeping the temperature at 20° C.+/-2° C. After 30 min. from the end of the addition an HPLC test is carried out to estimate the amount of the starting material that is smaller than 1percent compared to 3,5-di-O-benzoyl-2-C-methyl-D-ribopentono-1,4-lactone. 63 l of demineralised water is added in the reactor, the stirring is stopped and the layers are separated. The aqueous layer is eliminated and the organic phase, is concentrated to syrup. In another reactor 40 Kg of toluene is heated at 50° C. and then added to the syrup. The mixture is stirred for 1 hour then slowly cooled down to 20° C. It is filtered under vacuum and the panel is washed with 10.38 Kg of toluene and with 6 Kg of hexane. 11.2 Kg of 3,5-di-O-benzoyl-2-C-methyl-D-ribopentono-1,4-lactone is obtained. Yield=70percent. |
70 - 72% | With triethylamine; In acetonitrile; at 20℃; for 3.5h; | 100 g (0.617 moles) OF 2-C-METHYL-D-RIBOPENTONO-1, 4-lactone is added with stirring to 600 ml of acetonitrile, then 143 ml (1.23 moles) of benzoyl chloride is added in the suspension at room temperature. A mixture of 171 ml (1.23 moles) of triethylamine and 171 ml of acetonitrile is slowly (3 hours) dripped at room temperature. The reaction is stirred for 30 min. at room temperature, then an HPLC test is carried out. Thereafter 900 ml of water is added and oil is obtained. The oil is concentrated to syrup and the product crystallizes from hot toluene (490 ml). 160 g OF 3, 5-DI-O-BENZOYL-2-C-METHYL-D-RIBOPENTONO-1, 4-lactone is obtained as a white solid. Yield = 70percent. Pf : 110oC 1H (CDC13, 300 MHz): 8 ppm 5.41 (1H, d, H-3); 4.96 (1H, ddd, H-4); 4.66 (2H, system AB, CH2-5). 13 -NMR (CDC13, 300MHZ) : 8 ppm 174.59 (CO-1), 78.25 (C-4); 74.38 (C-3); 72.87 (C-2); 63.03 (C-5). |
70 - 72% | With triethylamine; In ethyl acetate; at 20℃; for 3.5h; | 20 g (0.12 moles) OF 2-C-METHYL-D-RIBOPENTONO-1, 4-lactone is added by stirring to 120 ml of ethyl acetate, then 27 ml (0.23 moles) of benzoyl chloride is added in the suspension at room temperature. A mixture of 32 ml (0.23 moles) of triethylamine and 32 ml of ethyl acetate is slowly (3 hours) dripped at room temperature cooling down to keep temperature lower then 20 C. The reaction is stirred for 30 min. at room temperature, and then an HPLC test is carried out. 180 ml of demineralised water is added, the organic phase is concentrated to a syrup and 3, 5-DI-O-BENZOYL-2-C-METHYL-D-RIBOPENTONO-1, 4-lactone crystallizes from 130 ml of toluene preheated at 50 C. 32 g of 3, 5-di-O-benzoyl-2-C- methyl-D-ribopentono-1, 4-lactone is obtained. Yield = 72percent. |
67% | With triethylamine; In acetone; at 20℃; for 3.5h; | 20 g (0.12 moles) of 2-C-methyl-D-ribopentono-1,4-lactone is added by stirring to 120 ml of acetone, then 27 ml (0.23 moles) of benzoyl chloride is added in the suspension at room temperature. A mixture of 32 ml (0.23 moles) of triethylamine and 32 ml of acetone is slowly (3 hours) dripped at room temperature cooling down to keep temperature lower then 20 C. The reaction is stirred for 30 min. at room temperature, and then an HPLC test is carried out. The salts are filtered, the solvent is evaporated and the 3,5-di-O-benzoyl-2-C-methyl-D-ribopentono-1,4-lactone crystallizes from 60 ml of toluene preheated at 50 C. 30 g of 3,5-di-O-benzoyl-2-C-methyl-D-ribopentono-1,4-lactone is obtained as a white solid. Yield=67percent. |
67% | With triethylamine; In acetone; at 20℃; for 3.5h; | 20 g (0.12 moles) of 2-C-methyl-D-ribopentono-1, 4-lactone is added by stirring to 120 ml of acetone, then 27 ML (0.23 moles) of benzoyl chloride is added in the suspension at room temperature. A mixture of 32 ml (0.23 moles) of triethylamine and 32 ml of acetone is slowly (3 hours) dripped at room temperature cooling down to keep temperature lower then 20 C. The reaction is stirred for 30 min. at room temperature, and then an HPLC test is carried out. The salts are filtered, the solvent is evaporated and the 3, 5-di-O-benzoyl-2- C-METHYL-D-RIBOPENTONO-1, 4-lactone crystallizes from 60 ml of toluene preheated at 50 C. 30 g of 3, 5-di-O-benzoyl-2-C-methyl-D-ribopentono-1, 4-lactone is obtained as a white solid. YIELD = 67percent. |
With triethylamine; In ethyl acetate;Cooling with ice; | General procedure: General procedure (A) for the acylation: 2-C-methyl-D-ribono-gamma-lactone 1 (1.62 g, 10.0 mmol) was suspended in ethyl acetate (20 mL), followed by the addition of acyl chloride (2.6 g, 20 mmol, 2 eq) under ice bath. To this solution was slowly added triethylamine (3.0 mL, 22 mmol, 2.2 eq), and the reaction mixture was stirred overnight. The insoluble substance was filtrated away, and washed with ethyl acetate (20 mL). The combined filtrate was washed with saturated NaHCO3 solution (20 mL), 1 M HCl (20 mL x 2) and brine (20 mL), respectively, then dried over Na2SO4 and concentrated. The obtained residue was purified by silca column chromatography or slurryed with toluene/petroleum ether to afford 2. |
Tags: 729596-46-7 synthesis path| 729596-46-7 SDS| 729596-46-7 COA| 729596-46-7 purity| 729596-46-7 application| 729596-46-7 NMR| 729596-46-7 COA| 729596-46-7 structure
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