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CAS No. : | 5117-19-1 | MDL No. : | MFCD00698694 |
Formula : | C16H34O9 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GLZWNFNQMJAZGY-UHFFFAOYSA-N |
M.W : | 370.44 | Pubchem ID : | 78798 |
Synonyms : |
|
Num. heavy atoms : | 25 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 22 |
Num. H-bond acceptors : | 9.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 88.94 |
TPSA : | 105.07 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -10.11 cm/s |
Log Po/w (iLOGP) : | 4.52 |
Log Po/w (XLOGP3) : | -2.18 |
Log Po/w (WLOGP) : | -0.91 |
Log Po/w (MLOGP) : | -2.21 |
Log Po/w (SILICOS-IT) : | 2.23 |
Consensus Log Po/w : | 0.29 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 0.69 |
Solubility : | 1810.0 mg/ml ; 4.88 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 0.5 |
Solubility : | 1180.0 mg/ml ; 3.2 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -3.34 |
Solubility : | 0.171 mg/ml ; 0.000461 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.49 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
91% | With dmap; triethylamine; In dichloromethane; for 3h;Cooling with ice; | A mixture of NEt3 (0.85 mL, 6.07 mmol), TsCl (1029 mg, 5.4 mmol) and DMAP (33 mg,0.27 mmol) were combined in CH2Clz (4 mL). This solution was cooled in an ice bath and to it was added <strong>[5117-19-1]octaethylene glycol</strong> (500 mg, 1.35 mmol). The reaction was stirred for 3hand was then concentrated in vacuum. Purification of the crude by flash chromatographyusing as eluent a mixture of cHex/ CH2Clz/MeOH (100/0/0 to 0/94/4) gave the desiredproduct as a colorless oil (m = 833 mg, 91 %). lH NMR (300 MHz, CD2Clz): o (ppm) 2.44(s, 6H), 3.54 (s, 8H), 3.57 (s, 8H), 3.58 (s, 8H), 3.64 (t, J = 4.7 Hz, 4H), 4.12 (t, J = 4.7 Hz,4H), 7.37 (d, J = 8.3 Hz, 4H), 7.78 (d, J = 8.3 Hz, 4H). MS: [M+NH4]+ m/z = 696. |
89% | With dmap; triethylamine; In dichloromethane; at 20℃; for 12h;Molecular sieve; Inert atmosphere; | ABT-2 (Scheme 52) was synthesized from commercially available<strong>[5117-19-1]octaethylene glycol</strong>. The diol (5g,0.Ol35moles) was dried for 24hours under vacuum while stirring with molecular sieves prior touse following which time, it was dissolved in anhydrous DCM(60m1) under nitrogen. To this solution was added dry Et3N (4.Sml, 0.O33moles) followed by TsC1 (7.Og, 0.04 moles) and finally DMAP (0.1645 g,0.OOl35moles). The reaction was allowed to proceed for 12 hours at room temperature at which time the solution was washed with 1N HC1 followed by an aqueous saturated sodium bicarbonate solution. The organic layers were combined, dried using sodium sulfate, concentrated in vacuo and the resulting oil purified by ISCO silica chromatography with a DCMIMeOH gradient. Bis-tosyl PEG-8 was isolated as a pale yellow oil in 89% yield (8g, 0.Ol2moles). Bis-tosyl PEG-8 (2g, 0.O029moles) was dissolved in 24m1 of a 1:1 DMF/DMSO solution to which Nal (0.153g ,0.O0lmoles) andNaN3 (1.34g, 0.O2lmoles) were added. The solution was left stirring at 60C over night, diluted in diethylether and extracted against brine and sodium bicarbonate. The organic layers were combined, dried using sodium sulfate and concentrated in vacuo to yield bis-azide PEG-8 in approx. 80 % crude yield (1.7g, 0.OO4moles). The bis-azide (1.2g, 0.0028 moles) was dissolved in 46 ml of methanol and reduced under an atmosphere of hydrogen in the presence of 10% PdJC. The reaction mixture was filtered through a celite plug, eluted with methanol, and concentrated to yield PEG8-diamine containing a significant amount of NaOMe but with sufficient purity to functionalize with DNP chloride. Peg8-diamine was acidified using 4M HCL indioxane and dried in vacuo to yield PEG8-diamine in 95% yield as the HCL salt(1 g, 0.OO27moles). The PEG8-diamine HCL salt (0.846g, 0.OO23moles) was neutralized with leq DIPEA and refluxed in lOml of EtOH to which small portions of DNP-Cl (0.465g, 0.O023moles total) were added over 5hr, diluted in DCM and washed with sodium bicarbonate and brine. Key intermediate iv was isolated as reddish oil in 69.5% yield (0.860g, 0.00 l6moles) and coupled directly to L 07 D-nipecotic acid (0.550g. 0.O024moles) in 50m1 DMIF in the presence of DIEPA (418ul, 0.O024moles) and HATU (0.912g, 0.O024moles) for Shr at room temperature. The solution was extracted against using brine/EtOAc and the organic layer concentrated in vacuo. The dark reddish oil was dissolved in 4M HClldioxane and stirred for 5hr at room temperature following which time the solution was concentrated to dryness under a stream of nitrogen and left overnight under vacuum. Crude (R or 5) ABT-2 was purified using HPLC (water/ACN 0.1% formic acid) to yield pure R or S-ABT-2 as theformate salt in 75% yield over 2 steps (0.64g. 0.00 l2moles). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; benzene; | EXAMPLE 3 <strong>[5117-19-1]octaethyleneglycol</strong> 3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionate A reaction flask was flushed with nitrogen and charged with 0.475 g of toluene sulfonic acid, 3 g of <strong>[5117-19-1]octaethyleneglycol</strong> (CARBOWAX 300), and 13.9 g of methyl 3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionate. The reaction mixture was stirred and heated at 125-130 C. for 4 hours after which it was cooled and dissolved in 500 ml of benzene, washed with water, and dried over Linde molecular sieve 4A. The reaction mixture was filtered and the benzene evaporated. The product was dissolved in 150 ml of methyl alcohol and extracted exhaustively with hexane. The methyl alcohol was stripped from the reaction product by vacuum distillation and the residue was dried at 80 C. at 0.52 mm pressure. In a similar fashion, nonobutyleneglycol (3-methyl-5-t-butyl-4-hydroxyphenyl)acetate can be prepared by substituting an equivalent amount of nonobutyleneglycol for <strong>[5117-19-1]octaethyleneglycol</strong> and substituting an equivalent amount of methyl (3-methyl-5-t-butyl-4-hydroxyphenyl)acetate for methyl 3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionate in the above procedure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
After stirring over the weekend, the reaction mixture was filtered through 3.5 g of fine SiO22 eluding with 95:5 CHCl3-CH3OH to give 227 mg of the tetraethyleneglycol ether as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33.1% | With pyridine; In tetrahydrofuran; at 20℃; | 3,6,9,12,15,18,21-Heptaoxatricosane-1,23-diol (5.5 g, 14.85 mmol) was dissolved in THF (30 mL). pyridine (3.73 mL, 46.2 mmol) was added to the mixture followed by 4-methylbenzene-1-sulfonyl chloride (2.84 g, 14.88 mmol). The mixture stirred at room temperature overnight. Mixture was concentrated by roto-vap. Residue was dissolved in dichloromethane, washed twice with saturated aqueous sodium bicarbonate. The combined aqueous layers were back-extracted with dichloromethane. The combined organics were washed twice with iN hydrochloric acid and once with brine. The organics were dried MgSO4, filtered, concentrated todryness to get 23-hydroxy-3 ,6,9, 12,15,18,21 -heptaoxatricosyl 4- methylbenzenesulfonate (2.58 g, 4.92 mmol, 33.1 % yield) which is used as is in the next step. Analysis condition D: Retention time = 1.41 mm; ESI-MS(+) m/z 525.3 (M + H) |
26% | With potassium iodide; silver(l) oxide; In dichloromethane; at 20℃; for 4h; | j00417j A solution of 3,6,9,12,15,18,21 -heptaoxatricosane- 1,23 -diol (3.2 g, 8.64 mmol) in DCM (50 mL) was charged with silver oxide (3 g, 12.97 mmol), potassium iodide (287 mg, 1.73 mmol) and portionwise addition of tosyl chloride (1.81 g, 9.51 mmol) and was stirred at room temperature for 4 h. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo resulting in a crude compound which was purified by chromatography on silica gel, eluting with 1-3% methanol in DCMto give 1.2 g, 26% yield ofthe title compound as pale yellow oil. ?H NMR (400 MHz, DMSO-d6): oe = 7.79 (d, J 8.3 Hz,2H), 7.48 (d, J= 8.0 Hz, 2H), 4.56 (t, J= 5.5 Hz, 1H), 4.07-4.15 (m, 2H), 3.57 (t, J= 4.4 Hz,4H), 3.47 -3.51 (m, 26H), 2.42 (s, 3H); MS (ESj: m/z = 524.30 [M+H] LCMS: tR =2.05mm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane;Inert atmosphere; | General procedure: 30 mg of the carotenoid succinate (1 equiv) was added to a solution of TEG/OEG (6 equiv) in 2 ml of dry CH2Cl2 under N2. To the red solution were added DMAP (3 equiv) and DCC (3 equiv) and the mixture stirred overnight. The reaction mixture should be kept in the dark and under N2. The reaction mixture was poured into Et2O (100 ml), dried, filtered and evaporated. The polar main product was separated by preparative TLC (Merck, Kieselgel 60, eluent n-hexane/acetone, 4:6) to give a red oily product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane;Inert atmosphere; | General procedure: 30 mg of the carotenoid succinate (1 equiv) was added to a solution of TEG/OEG (6 equiv) in 2 ml of dry CH2Cl2 under N2. To the red solution were added DMAP (3 equiv) and DCC (3 equiv) and the mixture stirred overnight. The reaction mixture should be kept in the dark and under N2. The reaction mixture was poured into Et2O (100 ml), dried, filtered and evaporated. The polar main product was separated by preparative TLC (Merck, Kieselgel 60, eluent n-hexane/acetone, 4:6) to give a red oily product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | General procedure: A solution of tetraethylen glycol (400 muL, 2.31 mmol) in THF (30 mL) was cooled to 0 C. After dropwise addition of KHMDS (0.5 M in toluene, 13.9 mL, 6.93 mmol) the mixture was stirred for 15 min. Subsequently, a solution of 13 (1.86 g, 6.93 mmol) in THF (8 mL) was added. After being stirred for 2 h at room temperature the mixture was treated with water and extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. After evaporation the crude product was purified by flash chromatography (hexane/EtOAc 1:1) to give 18a in 46% yield (620 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | General procedure: NaH (60% w/w in mineral oil, 3 equiv (for bis-propargylation) or 1.5 equiv (for mono-propargylation)) was added to a solution of appropriate diol 15ba-d or alcohol 19a-d (1 equiv) in anhydrous THF (0.2 M) at 0 C under an N2 atmosphere. A catalytic amount (spatula tip) of Bu4NI (0.05 equiv) and propargyl bromide (3 equiv (for bis-propargylation) or 1.5 equiv (for mono-propargylation)) was added sequentially. The mixture was stirred at rt overnight, before being concentrated under reduced pressure. Purification of the residue by flash column chromatography afforded diynes 16b-e and alkynes 9b-e as pale yellow oils. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With triethylamine; In dichloromethane; at 0 - 20℃; for 15h; | General procedure: TEA (0.62 mL, 4.43 mmol) was added to a 0C solution of 3,6,9,12,15-pentaoxaheptadecane-1,17-diol (500.0 mg, 1.771 mmol) in DCM (3.5 mL). Methanesulfonyl chloride (0.29 mL, 3.72 mmol) was added dropwise, and the mixture was allowed to gradually warm to rt. After 15 hr, the mixture was diluted with DCM, then successively washed with 1 N HCl (1 x 10 mL), water (2 x 10 mL), and saturated aqueous NaHCO3 (1 x 10mL). The organic phase was dried over MgSO4, filtered through paper, and concentrated to afford 54% yield of clear pale yellow oil. |
6.7 g | With dmap; triethylamine; In dichloromethane; at 0 - 20℃; | 50 ml of dichloromethane, 5.74 ml of triethylamine, 83 mg of p-dimethylaminopyridine and 5.0g of H-(OCH2CH2)8-OH (abbreviated as H-PEG8-OH) (Jiaxing Biomatrik, DH08150114) were successively added to areaction flask. A solution of 2.64 ml of methanesulfonyl chloride in 50 ml of dichloromethane was added dropwise withstirring at 0 C. After the completion of the dropwise addition, the reaction was stirred at room temperature overnight.The reaction solution was transferred to a separatory funnel and washed with dilute hydrochloric acid and brine successively.The organic layer was separated, dried with 30 g of anhydrous sodium sulfate. After the desiccant was filteredout, the organic layer was concentrated by rotary evaporation to obtain 8.17 g of crude product. The crude product waspurified by chromatography to obtain 6.7 g of pure product. 1H-NMR (400 MHz, CDC13), deltappm, 4.34-4.41 (4H, m),3.73-3.81 (4H, m), 3.60-3.71 (24H, m), 3.08 (6H, s). |
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Disposal | |
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Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
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H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
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H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
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H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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