alpha, oMega-Dipropionic acid triethylene glycol
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alpha, oMega-Dipropionic acid triethylene glycol
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CAS No:
31127-85-2
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Formula:
C12H22O8
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Chemical Name:
alpha, oMega-Dipropionic acid triethylene glycol
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Synonyms:
alpha, oMega-Dipropionic acid triethylene glycol;HOOC-PEG3-COOH;α,ω-Dipropionic acid triethylene glycol;4,7,10,13-Tetraoxahexadecanedioic acid;Bis-PEG4-acid;Bis-PEG5-acid;4,7,10,13-Tetraoxa-hexadecan-1,16-dicarbonsaeure;4,7,10,13-Tetraoxahexadecane-1,16-dioic acid
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CAS No:
alpha, oMega-Dipropionic acid triethylene glycol Use and Manufacturing
To a solution of compound 71(5.9 g, 20.05 mmol) in DMF (50 mL) were addedDIEA (3.6 mL, 20.67 mmol) and dropwise over 10 mm a solution of benzyl bromide(2.43 mL, 20.05 mmol) in DMF (50 mL). The reaction medium was stirred for 20 h atRT, quenched with 1 N HCI (500 mL) and extracted twice with EtOAc (200 mL). Thecombined organic phases were dried over Mg504, filtered, concentrated in vacuoand purified by two consecutive flash chromatographies on 400 g and 100 g of silicagel (gradient elution DCM/MeOH) to give 2.7 g of compound 72 as a pale green oil(35%).RMN 1H (300 MHz, oe in ppm, DMSO-d6): 2.42 (m, 2 H) ; 2.60 (t, J = 6.5 Hz, 2 H);3.47 (5, 6 H); 3.49 (5, 6 H); 3.59 (m, 2 H); 3.66 (d, J = 6.5 Hz, 2 H); 5.10 (5, 2 H);7.29 to 7.41 (m, 5 H).To compound 70 (8.05 g, 19.8 mmmol) was added formic acid (40 mL, 1.04 mol). The reaction medium was stirred for 1 d at RT, concentrated in vacuo and coevaporated with EtOAc (20 mL) to give 5.9 g of compound 71 as a colorless oil(quant.).RMN 1H (300 MHz, oe in ppm, DMSO-d6): 2.44 (t, J = 6.5 Hz, 4 H); 3.48 (5, 8 H); 3.50 (s, 4 H); 3.59 (d, J = 6.5 Hz, 4 H); 12.25 (broad m, 2 H).
Computed Properties
Molecular Weight:294.30
XLogP3:-1.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:15
Exact Mass:294.13146766
Monoisotopic Mass:294.13146766
Topological Polar Surface Area:112
Heavy Atom Count:20
Complexity:230
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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alpha, oMega-Dipropionic acid triethylene glycol
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