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Chemical Structure| 518044-32-1
Chemical Structure| 518044-32-1
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Product Details of [ 518044-32-1 ]

CAS No. :518044-32-1 MDL No. :MFCD11041117
Formula : C15H30O7 Boiling Point : -
Linear Structure Formula :- InChI Key :FJRDXEGYAVAMLB-UHFFFAOYSA-N
M.W : 322.39 Pubchem ID :11174684
Synonyms :

Safety of [ 518044-32-1 ]

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 [ 518044-32-1 ]

* 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.

  • Upstream synthesis route of [ 518044-32-1 ]
  • Downstream synthetic route of [ 518044-32-1 ]

[ 518044-32-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 112-60-7 ]
  • [ 1663-39-4 ]
  • [ 518044-32-1 ]
YieldReaction ConditionsOperation in experiment
82% With sodium In tetrahydrofuran at 20℃; To a solution of tetraethyleneglycol (40.61 mL; 45.64 g; 235 mmol) in abs. THF (125 mL) a piece of sodium (1/4 cm) was added. After the sodium had reacted completely, tert-butylacrylate (1 1.98 mL; 10.57 g; 82.5 mmol) was added dropwise over 20 min and the resulting solution was stirred at rt overnight. The pH was adjusted to 7-8 with NaOH solution (1 N) and the solvents were removed in vacuum. The residue was dissolved in sat. NaCl solution (75 mL) and extracted with EtOAc (3x100 mL). The combined organic layers were dried over MgSO4 and after evaporation of the solvent tert-butyl-15-hydroxy-4,7,10,13-tetraoxapentadecanoate (21.87 g; 67.8 mmol; 82percent based on tert-butylacrylate) was obtained as colorless oil. 1H-NMR (500 MHz, Chloroform-c/, TMS) δ [ppm] = 3.77 - 3.57 (m, 18H; OCH2); 3.01 (bs, 1 H, OH); 2.51 (t, 2H, J = 6.6 Hz, CH2COO'Bu); 1.45 (s, 9H, C(CH3)3); 13C{1H}-NMR (126 MHz, Chloroform-c/, TMS) δ [ppm] = 171.1 (COO); 80.7 (C(CH3)3); 72.6/70.8/70.7/70.6/70.5/67.0 (OCH2); 61.9 (HOCH2); 36.4 (CH2CO); 28.2 (C(CH3)3).
81%
Stage #1: With sodium In tetrahydrofuran at 20℃;
Stage #2: at 20℃;
[00162] Synthesis of tert-butyl l-hydroxy-3,6,9, 12-tetraoxapentadecan-15-oate (2): To a solution of tetraethylene glycol 1 (58.3 g, 300 mmol) in dry THF (200 mL) was added sodium (115 mg), and the mixture was stirred until sodium was consumed. To the resulting solution was then added tert-butyl acrylate (12.8 g, 100 mmol) in dry THF (50 mL) dropwise, and the resulting mixture was stirred overnight. The reaction was quenched with AcOH (0.1 mL) and water (0.5 mL) and stirred for 0.5 h, and was then extracted with ethyl acetate (200 mL χ 3). The combined organics were worked up by a standard procedure to give a clear oil product 2 (26 g, 81percent). ESI m/z: 340 (M+18)+.
81% With sodium In tetrahydrofuran at 20℃; To a solution of tetraethylene glycol (VI-1, 58 g, 0.30 mol) in dry THF (200 mL) was added sodium (0.12 g), and the mixture was stirred until the sodium was consumed. To the resulting solution was then added tert-butyl acrylate (VI-2, 13 g, 0.10 mol) in dry THF (50 mL) dropwise, and the resulting mixture was stirred at RT overnight. The reaction was quenched with acetic acid (0.1 mL) first and then water (0.5 mL), and the resulting mixture was stirred at RT for half an hour, and subsequently was extracted with ethyl acetate (3 x 200 mL). The combined organic solution was washed with water (30 mL) and then brine (3 x 100 mL), dried over sodium sulfate, filtered and concentrated to yield product (VI-3, 26 g, 81percent yield) as colorless oil. ESI m/z: 340 (M + 18)+
80% With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 20 h; To a solution of tetraethylene glycol (20.0 g, 103 mol) in anhydrous THF (54.0 mL) were added NaH (60percent dispersion in mineral oil, 42 mg, 1.05 mmol) and tert-butyl acrylate (5.2 mL, 36.0 mol). The resulting solution was stirred for 20 h at room temperature. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography (petroleum ether/EtOAc=1/1) to afford 16d-1 as a colorless oil (9.3 g, 80percent). IR (KBr) νmax 3445, 2873, 1729 cm-1. 1H NMR (400 MHz, CDCl3) δ (ppm) 3.65-3.53 (m, 18H), 2.43 (t, J=8.4 Hz, 2H), 1.37 (s, 9H). 13C NMR (100 MHz, CDCl3) δ (ppm) 170.7, 80.3, 72.6, 70.4 (2C), 70.3, 70.2, 70.1, 70.0, 66.7, 61.3, 36.0, 27.9 (3C). MS (ESI) m/z 340.2 [M+NH4]+. HRMS (ESI) m/z calcd for C15H30O7Na [M+Na]+: 345.1883; found, 345.1884.
77%
Stage #1: With sodium In tetrahydrofuran at 20℃; for 2 h;
Stage #2: at 20℃; for 24 h;
To dry tetraethylene glycol (17.2 mL, 0.10 mol) in dry tetrahydrofuran(100 mL), sodium (0.02 g, 0.87 mmol) was added. After 2 h, the sodium had dissolved and tert-butyl acrylate (4.35 mL, 0.03 mol) was added. The solution was stirred under exclusion of moisture for 24 h. After neutralisation with 1 M HCl (0.8 mL), the solvent was evaporated under reduced pressure. The residue was dissolved in brine(100 mL) and extracted three times with ethyl acetate (150 mL). The combined organic layers were washed with water (50 mL) and dried with MgSO4. The solvent was evaporated under reduced pressure to afford 2 as clear, pale yellow liquid; 4.3 g, 77percent; 1H NMR (300 MHz,CDCl3): 3.77–3.52 (m, 18H), 3.06 (s, 1H), 2.41 (t, J = 5.8 Hz, 2H), 1.40(s, 9H); ESI-MS m/z: [M + H]+ 323.20252.
36% With N-benzyl-trimethylammonium hydroxide In methanol at 20℃; To a flask containing PEG4 (3.88 g, 20 mmole) was added triton B (40percent solution in methanol, 1.08 mL, 0.25 mmole) and tert-butyl acrylate (3.62 mL, 24 mmole) followed after 15 min. The mixture was stirred at room temperature overnight. The mixture was concentrated in vacuo and the residue was purified by flash chromatography on silica gel with 1 percent methanol in dichloromethane as eluent to give the title compound as an colorless oil (2.35 g, 36percent). 1H NMR No. 1.45 (s, 9H), 2.5 (t, 2H), 3.65 (m, 18H).
23% With sodium In tetrahydrofuran at 20℃; for 24 h; To a solution of tetra (ethylene glycol) 11-1 (40.6 mL, 235 mmol) in 100 mL of tetrahedrofuran was added 47 mg of sodium. 12 mL of tert-butylacrylate was added after sodium was dissolved. The reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated in vacuo and quenched with 2 mL of 1 N HC1. The residue was suspended in brine and extracted with ethyl acetate (100 rriLXl, 50 mL X2). The organic layer was combined and washed with brine, dried over sodium sulfate and concentrated in vacuo to give 6.4 g (23percent) of compound 11-3.
23% at 20℃; for 24 h; Compound 2a: To a solution of tetra (ethylene glycol) (40.6 mL, 235 mmol) in 100 mL of tetrahydrofuran is added 47 mg of sodium. 12 mL of tert-butylacrylate is added after sodium is dissolved. The reaction mixture is stirred at room temperature for 24 hours. The reaction mixture is concentrated in vacuo and quenched with 2 mL of 1 N HCI. The residue is suspended in brine and extracted with ethyl acetate (100 mLX1 , 50 mL X2). The organic layer is combined and washed with brine, dried over sodium sulfate and concentrated in vacuo to give 6.4 g (23percent) of compound 2a.
23% With sodium In tetrahydrofuran at 20℃; for 24 h; Compound 11-3: To a solution of tetra (ethylene glycol) 11-1 (40.6 mL,235 mmol) in 100 mL of tetrahedrofuran was added 47 mg of sodium. 12 mL of tertbutylacrylatewas added after sodium was dissolved. The reaction mixture was stirred at roomtemperature for 24 hours. The reaction mixture was concentrated in vacuo and quenched with mL of 1 N HCI. The residue was suspended in brine and extracted with ethyl acetate (1 00mLXl, 50 mL X2). The organic layer was combined and washed with brine, dried oversodium sulfate and concentrated in vacuo to give 6.4 g (23percent) of compound 11-3.
23% With sodium In tetrahydrofuran at 20℃; for 24 h; To a solution of tetra (ethylene glycol) 11-1 (40.6 mL, 235 mmol) in100 mL oftetrahedrofuran was added 47 mg of sodium. 12 mL oftert-butylacrylate was added aftersodium was dissolved. The reaction mixture was stirred at room temperature for 24 hours. Thereaction mixture was concentrated in vacuo and quenched with 2 mL of 1 N HCl. The residue wassuspended in brine and extracted with ethyl acetate (100 mLXl, 50 mL X2). The organic layer was10 combined and washed with brine, dried over sodium sulfate and concentrated in vacuo to give 6.4 g(23percent) of compound 11-3.

Reference: [1] Synthetic Communications, 2004, vol. 34, # 13, p. 2425 - 2432
[2] Patent: WO2016/146638, 2016, A1, . Location in patent: Page/Page column 20
[3] Patent: WO2017/147542, 2017, A2, . Location in patent: Paragraph 00162
[4] Patent: WO2018/89373, 2018, A2, . Location in patent: Paragraph 0638-0639
[5] Tetrahedron, 2011, vol. 67, # 12, p. 2251 - 2259
[6] Journal of Medicinal Chemistry, 2004, vol. 47, # 20, p. 4802 - 4805
[7] Carbohydrate Research, 2007, vol. 342, # 3-4, p. 541 - 557
[8] Journal of Chemical Research, 2016, vol. 40, # 6, p. 368 - 370
[9] Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3259 - 3264
[10] Patent: WO2005/112919, 2005, A2, . Location in patent: Page/Page column 150
[11] Patent: WO2012/166560, 2012, A1, . Location in patent: Page/Page column 163; 168
[12] Patent: WO2013/68874, 2013, A1, . Location in patent: Page/Page column 20
[13] Patent: WO2013/192360, 2013, A1, . Location in patent: Paragraph 00458; 00479
[14] Patent: WO2013/185117, 2013, A1, . Location in patent: Paragraph 00444
[15] Synthetic Communications, 2007, vol. 37, # 11, p. 1899 - 1915
[16] Patent: CN107235848, 2017, A, . Location in patent: Paragraph 0021
  • 2
  • [ 112-60-7 ]
  • [ 1663-39-4 ]
  • [ 518044-32-1 ]
YieldReaction ConditionsOperation in experiment
73% With hydrogenchloride In tetrahydrofuran 15-Hydroxy-4,7,10,13-tetraoxapentadecanoic acid tert-butyl ester (9a)
To 300 mL of anhydrous THF was added 80 mg (0.0025 mol) of sodium metal and 128 mL of tetraethylene glycol 4a (0.94 mol) with stirring (Seitz and Kunz, J. Org. Chem., 62:813-826 (1997)).
After the sodium had completely dissolved, tert-butyl acrylate (24 mL, 0.33 mol) was added.
The solution was stirred for 20 hrs at room temperature and neutralized with 8 mL of 1.0 M HCl.
The solvent was removed in vacuo and the residue was suspended in brine (250 mL) and extracted with ethyl acetate (3*125 mL).
The combined organic layers were washed with brine (100 mL) then water (100 mL), dried over sodium sulfate, and the solvent was removed.
The resulting colorless oil was dried under vacuum to give 77.13 g (73percent yield) of product 9a ().
1H NMR: 1.40 (s, 9H), 2.49 (t, 2 H, J=6.4 Hz), 3.59-3.73 (m, 18 H).
Reference: [1] Patent: US2004/1838, 2004, A1,
  • 3
  • [ 518044-32-1 ]
  • [ 581065-95-4 ]
Reference: [1] Patent: WO2012/166560, 2012, A1,
[2] Patent: WO2013/192360, 2013, A1,
[3] Patent: WO2013/185117, 2013, A1,
[4] Journal of Chemical Research, 2016, vol. 40, # 6, p. 368 - 370
[5] Patent: WO2017/147542, 2017, A2,
[6] Patent: CN107235848, 2017, A,
[7] Patent: WO2018/89373, 2018, A2,
  • 4
  • [ 518044-32-1 ]
  • [ 663921-15-1 ]
Reference: [1] Journal of Chemical Research, 2016, vol. 40, # 6, p. 368 - 370
[2] Patent: WO2017/147542, 2017, A2,
[3] Patent: CN107235848, 2017, A,
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