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CAS No. : | 874208-91-0 | MDL No. : | MFCD20926396 |
Formula : | C16H32O9 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NOPQIPMESCUIHH-UHFFFAOYSA-N |
M.W : | 368.42 | Pubchem ID : | 57890897 |
Synonyms : |
|
Num. heavy atoms : | 25 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.94 |
Num. rotatable bonds : | 21 |
Num. H-bond acceptors : | 9.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 88.39 |
TPSA : | 101.91 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) : | -9.48 cm/s |
Log Po/w (iLOGP) : | 4.26 |
Log Po/w (XLOGP3) : | -1.31 |
Log Po/w (WLOGP) : | 0.21 |
Log Po/w (MLOGP) : | -1.55 |
Log Po/w (SILICOS-IT) : | 2.39 |
Consensus Log Po/w : | 0.8 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | 0.09 |
Solubility : | 450.0 mg/ml ; 1.22 mol/l |
Class : | Highly soluble |
Log S (Ali) : | -0.33 |
Solubility : | 172.0 mg/ml ; 0.466 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.44 |
Solubility : | 0.134 mg/ml ; 0.000364 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.47 |
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: |
* 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 |
---|---|---|
100% | With trifluoroacetic acid; In dichloromethane; at 20℃; | To a solution of compound 25 (1.04 g, 2.45 mmol) in DCM (15 mL) was added TEA (1.84 mL, 24.5 mmol). The reaction medium was stirred at RT overnight, concentrated in vacuo, diluted with DCM and co-evaporated with toluene (3 x) to give 1 g of compound 26 as a colorless oil (quant.). |
87% | With trifluoroacetic acid; at 20℃; | The tert-butyl ester (0.165 g, 0.0389 mmol) was deprotected by stirring at room temperature in trifluoroacetic acid (2.0 mL). The contents were then concentrated to a constant weight (0.125 g, 87%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; | The acid (0.660 g, 1.79 mmol) and N-hydroxysuccinimide (0.2278 g, 1.97 mmol) were dissolved in dry CH2Cl2 (15 mL). Ethyl dimethylaminopropyl carbodiimide hydrochloride (EDC, 0.343 g, 1.79 mmol) was added. After stirring at room temperature overnight, the reaction mixture was diluted with CH2Cl2 and was washed with water (2×45 mL). The organic layer was dried (MgSO4) and concentrated to a constant weight. The product was an oil (0.441 g, 53%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 60℃; for 3h; | To compound 26 (400 mg, 1.09 mmol) was added MsCI (1.27 mL, 16.3 mmol); the reaction medium was heated 3 h at 6000, concentrated in vacuo, diluted with DCM and concentrated in vacuo (3 x) to give 420 mg of compound 27 as a colorless oil(quant.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 24h; | To 2,5,8,11 , 14,17,20-heptaoxatricosan-23-oic acid (260 mg) in N^V-dimethylformamide (2.5 mL), was added 0-(7-azabenzotriazo -yl)-N,N,N,N-tetramethyluronium hexafluorophosphate (247 mg) and N-ethyl-N-isopropylpropan-2-amine (370 μ). The reaction was stirred for 3 minutes, and added to a solution of Example 43F (90 mg) and N-ethyl-N-isopropylpropan-2-amine (240 μL) in dimethylformamide (2.5 mL). The combined mixture was stirred for 24 hours. The mixture was diluted with 4 mL dimethylformamide/water 1/1, then chromatographed on a Grace Revelris system using aLuna 250 x 50 mm column, 5-60% acetonitrile in 0.1% aqueous trifluoroacetic acid over 30 minutes to give the title compound. MS (ESI) m/z 530.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.043 g | With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0℃; for 6h; | To a stirred solution of fulvestrant (0.100 g) and 2,5,8, 11, 14, 17, 20-heptaoxatricosan-23-oic acid (0.066 g) in dichloromethane (10 ml), DMAP (0.006 g) followed by DCC (0.051 g) was added at 0 C and stirred for 6 h. The reaction was monitored by TLC and LCMS. After completion of reaction, the reaction mixture was evaporated under vacuum to provide crude material. The crude material was purified using preparative HPLC using mobile phase A) 10 mM ammonium bicarbonate in water and B) acetonitrile. The fractions were lyophilized to provide (7R,8R,9S, l3S, l4S, l7S)-l7-hydroxy-l3-methyl-7-(9-((4,4,5,5,5- pentafluoropentyl)sulfmyl)nonyl)-7,8,9, 11 , 12, 13, 14, 15 , 16, 17-decahydro-6i7- cyclopenta[a]phenanthren-3-yl 2,5,8, 11,14, l7-hexaoxaicosan-20-oate (0.043 g) as a white semi solid. (0547) HPLC: 96.83% (0548) H NMR (400 MHz, DMSO): d 7.31 (d, 1H), 6.84 (d, 1H), 6.77 (s, 1H), 4.50 (d, 1H), 3.74 (t, 2H), 3.55-3.48 (m, 22 H), 3.42-3.40 (m,2H), 3.23 (s, 3H), 2.88-2.64 (m, 8H), 2.39-2.25 (m, 5H), 1.94- 1.79 (m, 4H), 1.71 (s, 1H), 1.62-1.48 (m ,4H), 1.38-1.18 (m, 18H), 0.90 (m, 1H) and 0.67 (s, 3H). |