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[ CAS No. 328898-40-4 ] {[proInfo.proName]}

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Chemical Structure| 328898-40-4
Chemical Structure| 328898-40-4
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Product Details of [ 328898-40-4 ]

CAS No. :328898-40-4 MDL No. :MFCD13194925
Formula : C41H71N3O8 Boiling Point : -
Linear Structure Formula :- InChI Key :HNDXPZPJZGTJLJ-UEJFNEDBSA-N
M.W : 734.02 Pubchem ID :24860548
Synonyms :

Safety of [ 328898-40-4 ]

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:

Application In Synthesis of [ 328898-40-4 ]

* 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.

  • Downstream synthetic route of [ 328898-40-4 ]

[ 328898-40-4 ] Synthesis Path-Downstream   1~21

  • 1
  • [ 110-89-4 ]
  • [ 1003024-02-9 ]
  • [ 328898-40-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In dichloromethane; acetonitrile at 78℃; for 2 - 2.5h; Heating / reflux; 1.E Potassium carbonate (1.8 kg), acetonitrile (16.7 kg), and piperidine (1.1 kg) were added to the product of Part D. The resulting mixture was then heated to 780C while distilling off dichloromethane. After solvent exchange to acetonitrile, the mixture was stirred at 2-2.5 hours at reflux, and then cooled to ambient temperature. Afterward, the residual potassium carbonate was filtered off, the filter cake was washed with acetonitrile (2.8 kg), and the solvent was distilled off under vacuum at a 5O0C jacket temperature. The resulting residue was dissolved in ethyl acetate (15.8 kg), and mixed with 0.5 N HCl (35.6 kg). The phases were separated at ambient temperature, and the lower aqueous phase was extracted three times with ethyl acetate (15.8 kg were used each time). The resulting aqueous phase was set to a pH of 11 by addition of 6 N NaOH (6.4 kg) and extracted three times with dichloromethane (18.7 kg each time) at ambient temperature. The combined lower organic phases were recharged to the reactor with sodium sulfate (5.3 kg). The mixture was then filtered to form a cake, which, in turn, was washed with dichloromethane (4.9 kg) and dried under vacuum at a jacket temperature of 5O0C to form a macro lide product. This product, in turn, was mixed with acetonitrile (21.7 L) and re-crystallized. The resulting crystals were isolated on a Nutsch filter, washed twice with cold acetonitrile (3.5 L each time), and dried under vacuum at 4O0C overnight to form macro lide (5) product. The composition of the product was confirmed using HPLC.
With potassium carbonate In tetrahydrofuran at 55 - 72℃; for 10h; 3.D Piperidine (0.55 kg per kg of product from Part B) was added to the product from Part C, followed by potassium carbonate (0.94 kg per kg of product from Part B). The resulting mixture was heated to 550C, and then maintained at that temperature for 3 hours while stirring. Afterward, the mixture was heated to 720C over 1 hour, and then stirred at that temperature for 6 hours. The composition of the product was analyzed using HPLC.
With potassium carbonate In xylene at 95 - 105℃; for 15h; 2 Potassium carbonate (0.94 kg), xylene (5 L), and piperidine (0.55 kg) are added to 1.0 kg of activated compound (1) made in accordance with the procedure in Part D. The resulting mixture is then heated to 95-1050C for 15 hours. Work-up includes dissolving the K2CO3 in water; removing excess piperidine; extracting into diluted HCl; extracting into tert-butyi methyl ether at a pH of 11; conducting a solvent switch to ethanol; and precipitating, isolating, and drying of the crude product. The product is then re- crystallized from methyl acetate or ethyl acetate. The composition of the product is confirmed using HPLC.
50.7 g With triethylamine at 40℃; for 8h; 1.D-1.E; 2.D-2.E; 3.D-3.E; 1.D-1.E; 2 Synthesis of 20,23-dipiperidinyl-5-O-mycaminosyl-tylonolide (V): add 50ml triethylamine and 50ml piperidine to the filtrate C, and heat to 40. After reacting for 8 hours, the temperature is lowered, then 200ml of phosphoric acid solution with a mass fraction of 10% is added, and after stirring for 30min, the pH is measured to be 6.52, stand still for layering, leaving the water phase; add 100ml of dichloromethane to the water phase for extraction and impurity removal. After standing for stratification, take the water phase; add 400ml ethyl acetate and 250ml sodium hydroxide solution with a concentration of 6mol/L to the water phase, stir for 30min and adjust the pH>13, stand for stratification, leave the oil phase; Add 400ml of water to wash, and then add 100g of anhydrous sodium sulfate for drying. After suction filtration, filtrate D is obtained. The purity of the product in filtrate D is 92.1%.using a standard curve to quantify, it is determined that the filtrate D contains 72.1g ( Yield 83.2%), the filtrate D was concentrated under normal pressure until the final total mass of the solution was 213.4g, and then slowly cooled, when the temperature dropped to 50°C, a large amount of solids precipitated, continue to cool to 30°C, and then stir for 5h; After suction filtration, the filter cake was dried under negative pressure to obtain 65.3g of the crude product of Tedilogen; then transfer the crude product to a three-necked flask, add 178.9g of acetonitrile, warm up to reflux temperature, stir for 2h, and filter while hot; the filtrate is slowly cooled down and the temperature is When it fell to 55°C, a large amount of solids precipitated. Continue to cool down to 30°C, then stir for 5 hours, filter with suction, and dry the filter cake under negative pressure to obtain 50.7g of Tydiluoxin (yield 58.5%). The purity of the finished product is determined to be 99.12. %, the content is 99.26%.

  • 2
  • tylosin tartrate [ No CAS ]
  • [ 328898-40-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen bromide / water / 7 h / 35 - 50 °C 2: sodium nitrite; acetic anhydride; acetic acid / 15 - 20 °C 3: formic acid / cyclohexane / Reflux
  • 3
  • [ 110-89-4 ]
  • C31H49NO10 [ No CAS ]
  • [ 328898-40-4 ]
YieldReaction ConditionsOperation in experiment
87.2% With formic acid In cyclohexane Reflux; 3.3 (3) preparation of (IV) extreme Luo Xin To the step (2) containing 20g of the 14-aldehyde group-5-0- carbon mildew amine sugar base -medicine lactone (33.6mmol) adding solution 17.1g piperidine (201.6mmol), 9.3g water-free formic acid (201.6mmol), heating to reflux, thermal insulation reaction 4-6h, detection to the raw content is less than 0.5%, stop heating, and cooling down to room temperature, adding 100 ml cyclohexane, stir until a solid precipitated, the supernatant is poured out, adding 40 ml water and 60 ml of methylene chloride, stirring after resting liquid separating, the aqueous phase used 5mol/L the pH of the solution to adjust NaOH 10-11 rear, with 60 ml dichloromethane extraction secondary, combined with the phase, with 80 ml water to neutral, after drying of organic phase is concentrated to dry, normal heptane pulping, filtering, drying, obtain 21.5g extreme Luo Xin, yield 87.2%.
  • 4
  • [ 110-89-4 ]
  • C38H57NO12S [ No CAS ]
  • [ 328898-40-4 ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: piperidine; C38H57NO12S With formic acid In ethanol for 4h; Reflux; Stage #2: With sodium hydrogencarbonate In ethyl acetate for 8h; Reflux; 1.3 preparation of tildipirosin reaction product 15 g was dissolved in 200 mL of ethanol, and 2. l of piperidine, 1.5 g of formic acid was added, and the temperature was raised to reflux State and heat for 4 hours, the liquid phase to complete the reaction after the rotation of dry ethanol, with 200mL ethyl acetate dissolved, respectively, by adding 7.7g carbon Sodium hydrogen phosphate, 3g piperidine, heated to reflux and heat for 8 hours, the liquid phase after the reaction is completely filtered, the filtrate and 200mL water, With a mass fraction of 10% hydrochloric acid to adjust the pH to 2 ~ 3, extraction layer, the water layer were washed with 200mL ethyl acetate 2 times, with The sodium hydroxide solution with a mass fraction of 30% was adjusted to pH 9 to 10 with solid precipitated, filtered and dried to give 12.8 g of a white solid with an HPLC purity of 98.5%, an isomer of 0.8% and a total molar Rate was 69.6%.
  • 5
  • tylosin tartrate [ No CAS ]
  • [ 328898-40-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogenchloride / water / 3 h / 55 °C 2.1: triethylamine / 3 h / Reflux 3.1: formic acid / ethanol / 4 h / Reflux 3.2: 8 h / Reflux
  • 6
  • [ 110-89-4 ]
  • 20,23-diiodo-5-O-mycaminosyl tylonolide [ No CAS ]
  • [ 328898-40-4 ]
YieldReaction ConditionsOperation in experiment
72.5% With potassium carbonate In dichloromethane at -5 - 45℃; for 5h; 6.1; 6.2; 6.3 A method for synthesizing 20,23-dipiperidin-5-O-mycaminosyl-tylonolide, the steps are as follows: 1. Add 300 mL of dichloromethane to a stoppered three-necked flask at a low temperature of -5 to 0 ° C, and then add 50 g of the 20,23-diiodo-5-O-mycodomyl glycosyl group prepared in Example 1. - telolactone, 120g piperidine and 210g K2CO3,Turn on the stirring, heat to 45 ° C and reflux for 5 h. After the reflux is completed,The resulting mixed system is filtered to remove K2CO3,Add 250 mL of pure water to the filtrate and stir for 30 min.The layer is allowed to stand, separated, and the organic layer is removed from the water layer;2. Add 250 mL of pure water to the organic phase, adjust the pH to 2 with 750 mL of 2 mol/L hydrochloric acid solution, stir for 30 minutes, let stand for stratification, separate the aqueous layer, and cool the aqueous layer to 0 ° C with 6 mol / L NaOH solution adjusts the pH to 8.0, staticThe layers were separated, the aqueous phase was separated, and the aqueous phase was extracted twice with 250 mL of dichloromethane.The organic layers were combined, dried over anhydrous Na2SO4, filtered and evaporated.Obtaining 48.63 g of 20,23-dipiperidinyl-5-O-mycaminosyl-tylonol solid crude;3. Dissolve the crude 20,23-dipiperidinyl-5-O-mycaminosyl-tylonolide in acetonitrile, place it in the refrigerator, and precipitate solids until the precipitate is complete. Filter and filter the cake. Rinse with acetonitrile and dry at 40 ° C overnight.Got 32.38g20,23-dipiperidinyl-5-O-mycaminosyl-tylonolide white solid, that is, Taidi Luoxin.Total yield: 72.50%; color: white; purity: 94.79%.
72.5% With potassium carbonate In dichloromethane at -5 - 45℃; for 5h; 6.1; 6.2; 6.3 Example 6A method for synthesizing 20,23-dipiperidin-5-O-mycaminosyl-tylonolide, the steps are as follows 1, at low temperature -5-0 ° C,Add 300 mL of dichloromethane to the stoppered three-necked flask.50 g of 20,23-diiodo-5-O-mycaminosyl-tylonolide prepared in Example 1,120g piperidine and 210g K2CO3, start stirring,Heat to 45 ° C and reflux for 5 h, after the reflux is completed,The resulting mixed system is filtered to remove K2CO3,Add 250 mL of pure water to the filtrate.Stir for 30min, let stand for separation, separate,The organic layer is removed from the water layer;2. Re-add 250 mL of pure water to the organic phase.Adjust the pH to 2 with 750 mL 2mol/L hydrochloric acid solution.Stir for 30 minutes, let stand for stratification, and separate the water layer.Cool the water layer to 0 ° C,Adjust the pH to 8.0 with 6mol/L NaOH solution.The layer is allowed to stand and the aqueous phase is separated.The aqueous phase was extracted twice with 250 mL of dichloromethane.The organic layers were combined and dried over anhydrous Na 2 SO 4Filter and concentrate to dryness,Obtaining 48.63 g of 20,23-dipiperidinyl-5-O-mycaminosyl-tylonol solid crude;3. Dissolve the crude 20,23-dipiperidinyl-5-O-mycaminosyl-tylonolide in acetonitrile, place it in the refrigerator, and precipitate solids until the precipitate is complete. Filter and filter the cake. Rinse with acetonitrile and dry at 40 ° C overnight to give 32.38 g20,23-dipiperidinyl-5-O-mycaminosyl-tylonolide white solid,ie tedicol
  • 7
  • [ 110-89-4 ]
  • [ 66767-27-9 ]
  • [ 328898-40-4 ]
YieldReaction ConditionsOperation in experiment
43.78% Stage #1: (11E,13E)-(4R,5S,6S,7R,9R,15R,16R)-6-((2R,3R,4S,5S,6R)-4-Dimethylamino-3,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-16-ethyl-4-hydroxy-7-(2-hydroxy-ethyl)-15-hydroxymethyl-5,9,13-trimethyl-oxacyclohexadeca-11,13-diene-2,10-dione With 1-methyl-1H-imidazole; triphenylphosphine In dichloromethane at -5 - 0℃; for 0.666667h; Stage #2: With iodine In dichloromethane at -5 - 5℃; for 8h; Stage #3: piperidine With potassium carbonate In dichloromethane at 45℃; for 5h; 9.3; 9.4; 9.5 3. Dissolve 100g of intermediate in 600mL of dichloromethane at low temperature -5-0 °C, add 50g of triphenylphosphine and 62g of methylimidazole under stirring, stir for 40min, slowly add 100g of iodine in 10 times, keep The temperature in the reaction system is not higher than 5°C, after the addition, maintain the low temperature -5-0 °C reaction for 8h, after the reaction is completed,The obtained mixture was quenched by adding 650 mL of an aqueous Na2SO3 solution.Stir for 30 min, let stand for layering, and separate the organic layer.240 g of piperidine and 420 g of K2CO3 were added to the organic layer, and stirring was started.After heating to 45 ° C and refluxing for 5 h, after the completion of the reflux, the resulting mixed system was filtered to remove K 2 CO 3 , 500 mL of pure water was added to the filtrate, stirred for 30 min, allowed to stand for separation, separated, and the aqueous layer was dehydrated to obtain an organic phase;4. Add 500 mL of pure water to the organic phase, adjust the pH to 3 with 1500 mL of 2 mol/L hydrochloric acid solution, stir for 30 minutes, let stand for stratification, separate the aqueous layer, and cool the aqueous layer to 0 ° C with 6 mol / LNaOH solution adjusts the pH to 8,The mixture was allowed to stand for stratification, and the aqueous phase was separated. The aqueous phase was extracted twice with 500 mL of dichloromethane. The organic layer was combined, dried over anhydrous Na?Concentrated to dryness, get 72.8g20,23-dipiperidinyl-5-O-mycaminosyl-tylonolide solid crude;5. Dissolve the crude 20,23-dipiperidinyl-5-O-mycaminosyl-tylonolide in acetonitrile, place it in the refrigerator, and precipitate solids until the precipitate is complete. Filter and filter the cake. The mixture was rinsed with cold acetonitrile and dried under vacuum overnight at 40 ° C to afford 62.4 g of 20,23-dipiperidinyl-5-O-mycaminosyl-tylorolide as a white solid. Total yield: 43.78%; color: white; purity: 96.37%.
  • 8
  • tylosin phosphate [ No CAS ]
  • [ 328898-40-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol / 3 h / Inert atmosphere; Cooling with ice 2.1: sulfuric acid / 3 h / 50 °C / pH 2 3.1: 1-methyl-1H-imidazole; triphenylphosphine / dichloromethane / 0.67 h / -5 - 0 °C 3.2: 8 h / -5 - 5 °C 3.3: 5 h / 45 °C
Multi-step reaction with 4 steps 1.1: sodium tetrahydroborate; methanol / 3 h / Inert atmosphere; Cooling with ice 2.1: sulfuric acid / 3 h / 50 °C / pH 2 3.1: pyridine; triphenylphosphine / dichloromethane / 0.67 h / -5 - 0 °C 3.2: 1 h / -5 - 5 °C 4.1: potassium carbonate / dichloromethane / 5 h / -5 - 45 °C
  • 9
  • C46H79NO17 [ No CAS ]
  • [ 328898-40-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sulfuric acid / 3 h / 50 °C / pH 2 2.1: 1-methyl-1H-imidazole; triphenylphosphine / dichloromethane / 0.67 h / -5 - 0 °C 2.2: 8 h / -5 - 5 °C 2.3: 5 h / 45 °C
Multi-step reaction with 3 steps 1.1: sulfuric acid / 3 h / 50 °C / pH 2 2.1: pyridine; triphenylphosphine / dichloromethane / 0.67 h / -5 - 0 °C 2.2: 1 h / -5 - 5 °C 3.1: potassium carbonate / dichloromethane / 5 h / -5 - 45 °C
  • 10
  • [ 110-89-4 ]
  • tylosin phosphate [ No CAS ]
  • [ 328898-40-4 ]
YieldReaction ConditionsOperation in experiment
43.78% Stage #1: tylosin phosphate With aluminum isopropoxide In butanone for 10h; Cooling with ice; Inert atmosphere; Stage #2: With formic acid In methanol at 50℃; for 24h; Stage #3: piperidine Further stages; 9.1; 9.2; 9.3; 9.4; 9.5 Example 9a method for synthesizing 20,23-dipiperidin-5-O-mycaminosyl-tylonolide,Proceed as follows: 1. In a 1000 ml three-necked flask,Dissolve 300 g of tylosin phosphate in 700 ml of methyl ethyl ketone,The three-necked flask was placed in an ice bath to cool.At the same time, nitrogen gas was introduced into the three-necked flask to make it under a nitrogen atmosphere, and 50 g of aluminum isopropoxide was slowly added under stirring.The reaction was stirred for 10 hours. After the reaction was completed, the nitrogen gas was stopped, and the three-necked flask was cooled to 30 ° C to obtain a mixed product.Object.2. Add 85 wt% formic acid solution to the three-necked flask containing the mixed product, adjust the pH of the system to 2, and raise the temperature to 50 °C.The mixture was hydrolyzed for 24 hours to obtain a crude intermediate.The crude intermediate was diluted with 1000 ml of water and 1400 ml of dichloromethane, and 5 mol/L sodium hydroxide solution was added thereto under stirring to adjust the pH to 6.5, and the layer was allowed to stand, and the lower aqueous phase was taken.Add fresh dichloromethane to the aqueous phase.With stirring, 5 mol/L sodium hydroxide solution was added to adjust the pH to 9.5, and the layer was allowed to stand to obtain an aqueous layer and an organic layer.The aqueous layer was extracted twice with 700 mL of dichloromethane.The organic phase obtained by the two extractions and the organic layer were combined, dried over magnesium sulfate, filtered, and the filtrate was evaporated under reduced pressure to remove organic solvent to give 152.8 g of a foamy solid.The foamy solid was dissolved in 500 mL of t-butyl methyl ether.The crystals were precipitated by stirring at room temperature, and the precipitate was collected.The precipitate was rinsed with 141 mL of cold tert-butyl methyl ether and dried.This gave 139.8 g of a white solid intermediate.3. Dissolve 100g of the intermediate in 600mL of dichloromethane at a low temperature of -5-0 °C.50 g of triphenylphosphine and 62 g of methylimidazole were added with stirring.After stirring for 40 minutes, 100 g of iodine was slowly added in 10 portions.Keep the temperature inside the reaction system not higher than 5 ° C,After the addition, the reaction was maintained at a low temperature of -5-0 ° C for 8 h. After the reaction was completed,To the resulting mixture was added 650 mL of an aqueous Na2SO3 solution.After quenching, stirring for 30 min, standing layering, separating the organic layer, adding 240 g of piperidine and 420 g of K2CO3 to the organic layer.The stirring was started, heated to 45 ° C and refluxed for 5 h. After the reflux was completed, the obtained mixed system was filtered to remove K 2 CO 3 .Add 500 mL of pure water to the filtrate and stir for 30 min.The layer is allowed to stand, separated, and the organic layer is removed from the water layer;4,Re-add 500 mL of pure water to the organic phase.Adjust the pH to 3 with 1500 mL 2mol/L hydrochloric acid solution.Stir for 30 minutes, let stand for stratification, and separate the water layer.Cool the water layer to 0 ° C,Adjust the pH to 8 with a 6 mol/L NaOH solution.The layer is allowed to stand and the aqueous phase is separated.The aqueous phase was extracted twice with 500 mL of dichloromethane.The organic layers were combined and dried over anhydrous Na 2 SO 4Filter and concentrate to dryness,Obtaining 72.8 g of 20,23-dipiperidinyl-5-O-mycaminosyl-tylonol solid crude;5,The crude 20,23-dipiperidinyl-5-O-mycaminosyl-tylonolide was dissolved by heating with acetonitrile, and placed in a refrigerator, and a solid precipitated.Until the precipitation was complete, the filter cake was rinsed with cold acetonitrile and dried under vacuum at 40 ° C overnight.Get 62.4g20,23-Dipiperidinyl-5-O-mycaminosyl-tylonolide white solid, ie tedicol.Total yield: 43.78%; color: white; purity: 96.37%.hehDefinitions of henouna male; a man.is that a he or a she?pronounused to refer to a man, boy, or male animal previously mentioned or easily identified.everyone liked my father-he was the perfect gentlemanSee alsoHe, HE, he is, who is he, he says, he also, that he, he man, he falls, he is out, he is ten years old, he deserves itTranslations of hepronounhe, himhe, sheits, their, it, his, that, henounman, male, he, husband, menfolk, menfolksboy, heman, male, heboy, heyoung people, young, youth, he
  • 11
  • [ 328898-40-4 ]
  • [ 107-92-6 ]
  • C53H89N3O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 12.0833h; 48.5 Example 48. Formation of Butyric and Isobutyric esters of ALCs
Method 5: General procedure: Carboxylic acid (180 mg, 2.04 mmol) was solved in 3 mL dichloromethane. Under stirring conditions 4-Dimethylaminopyridine (274 mg, 2.24 mmol) and A-16 were added. The reaction solution was cooled to 0°C and N,N'-Dicyclohexylcarbodiimide (463 mg, 2.24 mmol) was added. The reaction was stirred continually at this temperature for 5 min and then progressively warmed to room temperature where it was stirred for 12h. Precipitation was removed via filtration. The reaction was washed with a saturated solution of NaHCO3 (3x) and dried over anhydrous Na2SO4. The solvent was evaporated in vacuo. Product was solved in methanol and water was added. Solution was cooled to - 20°C, a precipitation occurred which was extracted and dried in vacuo.
  • 12
  • [ 1468-39-9 ]
  • [ 328898-40-4 ]
  • C46H79N3O9 [ No CAS ]
  • C51H87N3O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane at 20℃; Overall yield = 87 %; 50.2A Example 50. Formation of Isovaleric esters of ALCs
Method 2A. General procedure: The ALC was taken up in DCM. To this were added pyridine and isovaleric acid anhydride (1 equiv. pyridine/1 equiv. isovaleric acid anhydride). The mixture was stirred at room overnight or over the weekend and was then poured on an aqueous citric acid solution (5 % or 10 %) at RT and was stirred for 15 min. The aqueous phase was extracted with EtOAc (2 x) and was afterwards brought to pH = 8 with solid Na2CO3. The alkaline aqueous layer was extracted with EtOAc (2x) and the combined organic phases were washed with water (1 x) and saturated aqueous NaCl-solution (1 x), dried (Na2SO4), concentrated to dryness and dried at the oil pump. Products were obtained as colorless solids or foams.
  • 13
  • [ 328898-40-4 ]
  • [ 142-62-1 ]
  • C47H81N3O9 [ No CAS ]
  • C53H91N3O10 [ No CAS ]
  • C59H101N3O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Cooling with ice; Overall yield = 56 %; 51 Example 51. Long chain (>C5) fatty acid substation of Tildipirosin Hexanoic acid (290 mg, 2.5 mmol) was taken up in 5 mL dichloromethane (DCM). Compound A-16 (367 mg, 0.5 mmol) and 4-Dimethylaminopyridine (DMAP) (336 mg, 2.75 mmol) were added and the resulting solution was cooled in an ice bath for approximately 10 minutes. At this point, dicyclohexylcarbodiimide (DCC) (567 mg, 2.75 mmol) was added slowly. The reaction was stirred continually at this temperature for 5 minutes and then progressively warmed to room temperature where it was stirred overnight. Dicyclohexylurea (DCU) that was formed during the reaction is filtered off and discarded. The filtrate was collected and then washed with a saturated solution of ammonium chloride (3x), sodium hydrogencarbonate (3x), water (1x) and dried over anhydrous Na2SO4. The solvent was evaporated in vacuo. This was followed by re- dissolving the residue in a small volume of methanol. The solution was transported dropwise into ice-cold water (2x volume of methanol) and stored in the freezer overnight. The precipitated product was filtered off and dried under high-vacuum to produce a mixture of E-437, E-438 and E-439 (56%).
  • 14
  • [ 124-07-2 ]
  • [ 328898-40-4 ]
  • C65H113N3O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Cooling with ice; 51 Example 51. Long chain (>C5) fatty acid substation of Tildipirosin Hexanoic acid (290 mg, 2.5 mmol) was taken up in 5 mL dichloromethane (DCM). Compound A-16 (367 mg, 0.5 mmol) and 4-Dimethylaminopyridine (DMAP) (336 mg, 2.75 mmol) were added and the resulting solution was cooled in an ice bath for approximately 10 minutes. At this point, dicyclohexylcarbodiimide (DCC) (567 mg, 2.75 mmol) was added slowly. The reaction was stirred continually at this temperature for 5 minutes and then progressively warmed to room temperature where it was stirred overnight. Dicyclohexylurea (DCU) that was formed during the reaction is filtered off and discarded. The filtrate was collected and then washed with a saturated solution of ammonium chloride (3x), sodium hydrogencarbonate (3x), water (1x) and dried over anhydrous Na2SO4. The solvent was evaporated in vacuo. This was followed by re- dissolving the residue in a small volume of methanol. The solution was transported dropwise into ice-cold water (2x volume of methanol) and stored in the freezer overnight. The precipitated product was filtered off and dried under high-vacuum to produce a mixture of E-437, E-438 and E-439 (56%).
  • 15
  • [ 334-48-5 ]
  • [ 328898-40-4 ]
  • C61H107N3O10 [ No CAS ]
  • C71H125N3O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Cooling with ice; Overall yield = 41 %; 51 Example 51. Long chain (>C5) fatty acid substation of Tildipirosin Hexanoic acid (290 mg, 2.5 mmol) was taken up in 5 mL dichloromethane (DCM). Compound A-16 (367 mg, 0.5 mmol) and 4-Dimethylaminopyridine (DMAP) (336 mg, 2.75 mmol) were added and the resulting solution was cooled in an ice bath for approximately 10 minutes. At this point, dicyclohexylcarbodiimide (DCC) (567 mg, 2.75 mmol) was added slowly. The reaction was stirred continually at this temperature for 5 minutes and then progressively warmed to room temperature where it was stirred overnight. Dicyclohexylurea (DCU) that was formed during the reaction is filtered off and discarded. The filtrate was collected and then washed with a saturated solution of ammonium chloride (3x), sodium hydrogencarbonate (3x), water (1x) and dried over anhydrous Na2SO4. The solvent was evaporated in vacuo. This was followed by re- dissolving the residue in a small volume of methanol. The solution was transported dropwise into ice-cold water (2x volume of methanol) and stored in the freezer overnight. The precipitated product was filtered off and dried under high-vacuum to produce a mixture of E-437, E-438 and E-439 (56%).
  • 16
  • [ 328898-40-4 ]
  • [ 802294-64-0 ]
  • C44H75N3O9 [ No CAS ]
  • C47H79N3O10 [ No CAS ]
  • C50H83N3O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Cooling with ice; 5.4 Example 5
Method 4. General procedure: Propionic acid (4 eq) was taken up in 5 mL dichloromethane (DCM). Compound A-16 (0.5 mmol) and 4-dimethylaminopyridine (DMAP) (4.4 eq) were added and the resulting solution was cooled in an ice bath for approximately 10 minutes. At this point, dicyclohexylcarbodiimide (DCC) (4.4 eq) was added slowly. The reaction was stirred continually at this temperature for 5 minutes and then progressively warmed to room temperature where it was stirred overnight. Dicyclohexylurea (DCU) that was formed during the reaction is filtered off and discarded. The filtrate was collected and then washed with a saturated solution of sodium hydrogencarbonate (3x), water (1x) and dried over anhydrous Na2SO4. The solvent was evaporated in vacuo. This was followed by re- dissolving the residue in a small volume of methanol. The solution was transported dropwise into ice-cold water (2x volume of methanol) and stored in the freezer overnight. The precipitated product was filtered off and dried under high-vacuum to produce
  • 17
  • [ 328898-40-4 ]
  • [ 64-19-7 ]
  • C47H77N3O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% Stage #1: 20,23-dipiperidin-5-O-mycaminosyl tylonolide; acetic acid With dmap In dichloromethane for 0.166667h; Cooling with ice; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 20℃; Cooling with ice; 47.3 Example 47. Formation of Acetic esters of ALCs
Method 3. Acetic acid (4 eq) was taken up in 5 mL dichloromethane (DCM). Compound A-16 (0.5 mmol) and 4-dimethylaminopyridine (DMAP) (4.4 eq) were added and the resulting solution was cooled in an ice bath for approximately 10 minutes. At this point, dicyclohexylcarbodiimide (DCC) (4.4 eq) was added slowly. The reaction was stirred continually at this temperature for 5 minutes and then progressively warmed to room temperature where it was stirred overnight. Dicyclohexylurea (DCU) that was formed during the reaction is filtered off and discarded. The filtrate was collected and then washed with a saturated solution of sodium hydrogencarbonate (3x), water (1x) and dried over anhydrous Na2SO4. The solvent was evaporated in vacuo. This was followed by re- dissolving the residue in a small volume of methanol. The solution was transported dropwise into ice-cold water (2x volume of methanol) and stored in the freezer overnight. The precipitated product was filtered off and dried under high-vacuum to produce a product.
  • 18
  • [ 110-89-4 ]
  • 23-deoxy-23-oxomycaminosyl tylonolide [ No CAS ]
  • [ 328898-40-4 ]
YieldReaction ConditionsOperation in experiment
65 g With formic acid In ethyl acetate at 70℃; for 2.5h; 2.2 (2) 62 g of 23-aldehyde-5-O-mycaminosyl-tylonolide was dissolved in ethyl acetate. Add formic acid, piperidine. The molar ratio of 23-aldehyde-5-O-mycaminosyl-tylonolide: formic acid: piperidine is 1:4:6. Then the mixture is heated to 70 ° C, reaction for 2.5 hours. After the reaction is finished, cooled to room temperature, 800 ml of water is added, and then adjusted with 1.5 N hydrochloric acid pH value to 3-4, layering, take the water phase, wash the ethyl acetate three times, then adjust the pH value to 10-11 by 6N sodium hydroxide, filter, add the filter cake to 10 times water, adjust the pH value to 3- 4, after dissolving, the pH value of sodium hydroxide is adjusted to 10-11, secondary crystallization, and the product 20,23-dipiperidinyl-5-O-mycaminosyl-tylonolide 65g, The product HPLC purity was 98%.
  • 19
  • tylosin tartarate [ No CAS ]
  • [ 328898-40-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen bromide / water / 5 h / 50 - 55 °C 2: Dess-Martin periodane / dichloromethane / 0 °C 3: formic acid / ethyl acetate / 2.5 h / 70 °C
  • 20
  • tylosin phosphate [ No CAS ]
  • [ 328898-40-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: formic acid / ethyl acetate / 5 h / 75 °C 2.1: water / 5 h / 68 °C 3.1: triphenylphosphine; pyridine / dichloromethane / 0.5 h / 20 °C 3.2: 1 h 4.1: triethylamine / 8 h / 40 °C
  • 21
  • [ 1003024-00-7 ]
  • [ 328898-40-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: water / 5 h / 68 °C 2.1: triphenylphosphine; pyridine / dichloromethane / 0.5 h / 20 °C 2.2: 1 h 3.1: triethylamine / 8 h / 40 °C
Same Skeleton Products
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