Structure of Mpeg5-n3
CAS No.: 1202681-04-6
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| CAS No. : | 1202681-04-6 |
| Formula : | C11H23N3O5 |
| M.W : | 277.32 |
| SMILES Code : | COCCOCCOCCOCCOCCN=[N+]=[N-] |
| English Name : | 16-Azido-2,5,8,11,14-pentaoxahexadecane |
| MDL No. : | MFCD31656928 |
* 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 |
|---|---|---|
| 73% | With sodium azide In N,N-dimethyl-formamide at 80℃; for 11.5h; Inert atmosphere; | |
| 57% | With sodium azide In N,N-dimethyl-formamide at 80℃; for 11.5h; | 6 [Example 6: Synthesis of compound of the present invention 5] Compounds of the present invention having a PEG chain were synthesized in the same manner as in Example 5. Compound 28 (2-(2-(2-methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate) was synthesized from Compound 27 as previously reported ()). Compound 29 (2,5,8,11,14-pentaoxahexadecan-16-ol) was synthesized from Compound 28 as previously reported ()). Compound 30 (2,5,8,11,14-pentaoxahexadecan-16-yl 4-methylbenzenesulfonate) was synthesized from Compound 29 as previously reported ()). To a stirring solution of Compound 30 (813 mg, 2 mmol) in DMF (2 mL), NaN3 (308 mg, 1.61 mmol) was added at room temperature. The reaction mixture was stirred at 80°C for 11.5 hours, and then concentrated under reduced pressure. A precipitate was filtered to obtain Compound 31 (16-azido-2,5,8,11,14-pentaoxahexadecane) (355 mg, yield 57%) as a solid. 1H-NMR (400 MHz, CDCl3) δ 3.37-3.40 (m, 5H), 3.53-3.56 (m, 2H), 3.63-3.68 (m, 16H; 13C NMR (125 MHz, CDCl3) δ50.7, 59.0, 70.0, 70.6(7C), 71.9; HRMS (ESI), C11H23N3NaO5[M+H]+m/z calculated: 300.1530, found: 300.1526. |
| 57% | With sodium azide In N,N-dimethyl-formamide at 80℃; for 11.5h; | 6 [Example 6: Synthesis of compound of the present invention 5] Compounds of the present invention having a PEG chain were synthesized in the same manner as in Example 5. Compound 28 (2-(2-(2-methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate) was synthesized from Compound 27 as previously reported ()). Compound 29 (2,5,8,11,14-pentaoxahexadecan-16-ol) was synthesized from Compound 28 as previously reported ()). Compound 30 (2,5,8,11,14-pentaoxahexadecan-16-yl 4-methylbenzenesulfonate) was synthesized from Compound 29 as previously reported ()). To a stirring solution of Compound 30 (813 mg, 2 mmol) in DMF (2 mL), NaN3 (308 mg, 1.61 mmol) was added at room temperature. The reaction mixture was stirred at 80°C for 11.5 hours, and then concentrated under reduced pressure. A precipitate was filtered to obtain Compound 31 (16-azido-2,5,8,11,14-pentaoxahexadecane) (355 mg, yield 57%) as a solid. 1H-NMR (400 MHz, CDCl3) δ 3.37-3.40 (m, 5H), 3.53-3.56 (m, 2H), 3.63-3.68 (m, 16H; 13C NMR (125 MHz, CDCl3) δ50.7, 59.0, 70.0, 70.6(7C), 71.9; HRMS (ESI), C11H23N3NaO5[M+H]+m/z calculated: 300.1530, found: 300.1526. |
| With sodium azide In N,N-dimethyl-formamide at 50℃; for 12h; | ||
| 57 % | With sodium azide In N,N-dimethyl-formamide at 80℃; | 6 [Example 6: Synthesis of compound of the present invention 5] Compounds of the present invention having a PEG chain were synthesized in the same manner as in Example 5. Compound 28 (2-(2-(2-methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate) was synthesized from Compound 27 as previously reported ()). Compound 29 (2,5,8,11,14-pentaoxahexadecan-16-ol) was synthesized from Compound 28 as previously reported ()). Compound 30 (2,5,8,11,14-pentaoxahexadecan-16-yl 4-methylbenzenesulfonate) was synthesized from Compound 29 as previously reported ()). To a stirring solution of Compound 30 (813 mg, 2 mmol) in DMF (2 mL), NaN3 (308 mg, 1.61 mmol) was added at room temperature. The reaction mixture was stirred at 80°C for 11.5 hours, and then concentrated under reduced pressure. A precipitate was filtered to obtain Compound 31 (16-azido-2,5,8,11,14-pentaoxahexadecane) (355 mg, yield 57%) as a solid. 1H-NMR (400 MHz, CDCl3) δ 3.37-3.40 (m, 5H), 3.53-3.56 (m, 2H), 3.63-3.68 (m, 16H; 13C NMR (125 MHz, CDCl3) δ50.7, 59.0, 70.0, 70.6(7C), 71.9; HRMS (ESI), C11H23N3NaO5[M+H]+m/z calculated: 300.1530, found: 300.1526. |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With water; triphenylphosphine 1.) THF, RT, 12 h, 2.) RT, 12 h; Multistep reaction; | ||
| With palladium on activated charcoal; hydrogen In methanol at 20℃; for 2h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: pyridine / 0 °C 2: sodium azide / dimethylformamide / 12 h / 50 °C | ||
| Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 5 h / 20 °C / Inert atmosphere 2: sodium azide / N,N-dimethyl-formamide / 11.5 h / 80 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: 1.) PPh3, 2.) H2O / 1.) THF, RT, 12 h, 2.) RT, 12 h 2: 20 mM KH2PO4 / acetone / 2 h / Ambient temperature |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 4 steps 1: triethylamine; dmap / dichloromethane / 8 h / 20 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 15 h / 80 °C / Inert atmosphere 3: triethylamine; dmap / dichloromethane / 5 h / 20 °C / Inert atmosphere 4: sodium azide / N,N-dimethyl-formamide / 11.5 h / 80 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 15 h / 80 °C / Inert atmosphere 2: triethylamine; dmap / dichloromethane / 5 h / 20 °C / Inert atmosphere 3: sodium azide / N,N-dimethyl-formamide / 11.5 h / 80 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 2: triethylamine / dichloromethane / 15.5 h / 20 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 2: triethylamine / dichloromethane / 15.5 h / 20 °C / Inert atmosphere 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane; 1,2-dimethoxyethane / 2 h / 20 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 4 steps 1.1: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 2.1: triethylamine / dichloromethane / 15.5 h / 20 °C / Inert atmosphere 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane; 1,2-dimethoxyethane / 2 h / 20 °C / Inert atmosphere 4.1: sodium carbonate decahydrate / water; 1,4-dioxane / 1.5 h / 20 °C / Inert atmosphere 4.2: 12 h / 20 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 5 steps 1.1: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 2.1: triethylamine / dichloromethane / 15.5 h / 20 °C / Inert atmosphere 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane; 1,2-dimethoxyethane / 2 h / 20 °C / Inert atmosphere 4.1: sodium carbonate decahydrate / water; 1,4-dioxane / 1.5 h / 20 °C / Inert atmosphere 4.2: 12 h / 20 °C / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere |