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[ CAS No. 219989-84-1 ] {[proInfo.proName]}

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Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
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Chemical Structure| 219989-84-1
Chemical Structure| 219989-84-1
Structure of 219989-84-1 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 219989-84-1 ]

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Product Details of [ 219989-84-1 ]

CAS No. :219989-84-1 MDL No. :MFCD04307791
Formula : C27H42N2O5S Boiling Point : -
Linear Structure Formula :- InChI Key :FABUFPQFXZVHFB-PVYNADRNSA-N
M.W : 506.70 Pubchem ID :6445540
Synonyms :
BMS-247550;Aza-epothilone B;Azaepothilone BBMS 2475501. Trade name: Ixempra.

Calculated chemistry of [ 219989-84-1 ]

Physicochemical Properties

Num. heavy atoms : 35
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.74
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 144.19
TPSA : 140.29 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.42
Log Po/w (XLOGP3) : 3.62
Log Po/w (WLOGP) : 3.56
Log Po/w (MLOGP) : 1.22
Log Po/w (SILICOS-IT) : 4.78
Consensus Log Po/w : 3.32

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.24
Solubility : 0.00294 mg/ml ; 0.00000581 mol/l
Class : Moderately soluble
Log S (Ali) : -6.25
Solubility : 0.000282 mg/ml ; 0.000000557 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -5.09
Solubility : 0.00408 mg/ml ; 0.00000805 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 6.4

Safety of [ 219989-84-1 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P272-P280-P285-P302+P352-P304+P341-P333+P313-P342+P311-P363-P501 UN#:2811
Hazard Statements:H317-H334 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 219989-84-1 ]

* 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 [ 219989-84-1 ]
  • Downstream synthetic route of [ 219989-84-1 ]

[ 219989-84-1 ] Synthesis Path-Upstream   1~44

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YieldReaction ConditionsOperation in experiment
42.8% With 3,3-dimethyldioxirane In dichloromethane; acetone at -78 - -50℃; for 1.5 h; Inert atmosphere Preparation of Ixabepilone
To a 250-mL three-neck flask equipped with a stir bar was added 10.0 mL of deionized water, 10.0 mL of acetone and 2.50 g of NaHCO3.
The resulting mixture was stirred vigorously in a 24° C. bath for 15 minutes.
To this mixture was added 3 portions of potassium peroxymonosulfate (1.67 g) every 10-15 minutes under a reduced pressure (ca. 50-100 mmHg). DMDO was distilled out and obtained as an acetone solution after every addition of potassium peroxymonosulfate.
Under a N2 atmosphere, DMDO (10 mL) was transferred to the solution of Ia (61 mg, 0.124 mmol) in dry DCM (2.0 mL) slowly using a cannula while controlling the solution temperature at -78° C.
Then the reaction mixture was warmed up to -50° C. and stirred for 1.5 h.
When TLC analysis indicated the reaction was complete, excess DMDO was quenched by adding dimethyl sulfide (0.1 mL) at -50° C., and the mixture was warmed to room temperature and concentrated under reduced pressure.
The residue was purified by column chromatography on silica gel (EtOAc/n-heptane=2:1) to give ixabepilone (27 mg, yield: 42.8percent) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.00 (m, 1H), 6.96 (s, 1H), 6.55 (s, 1H), 4.66-4.64 (m, 1H), 4.43 (brs, 1H), 4.06-4.04 (m, 1H), 3.79 (m, 1H), 2.82-2.79 (m, 1H), 2.77 (brs, 1H), 2.69 (s, 3H), 2.52-2.39 (m, 2H), 2.48 (brs, 1H), 2.31-2.26 (dd, J=12.0, 4.0 Hz, 1H), 1.96 (t, J=8.0 Hz, 2H), 1.62-1.53 (m, 4H), 1.37 (m, 3H), 1.33 (s, 3H), 1.27 (s, 3H), 1.16 (d, J=4.0 Hz, 3H), 1.09 (s, 3H), 0.98 (d, J=8.0 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 220.8, 170.6, 165.0, 152.5, 138.0, 119.2, 116.0, 75.2, 73.6, 61.5, 61.2, 54.6, 52.7, 43.8, 40.4, 37.9, 31.9, 31.8, 30.7, 23.9, 23.0, 21.8, 21.0, 19.3, 17.3, 17.1, 14.4; LCMS 507.28 [M+H].
0.31 g With 3-chloro-benzenecarboperoxoic acid In chloroform at -20 - -15℃; for 4 h; Inert atmosphere Example-48: Preparation of (lS,3S,7S,10R,HS,12S,16R)-7,ll-dihydroxy- 8,8,10,12,16-pentamethyl-3-[(lE)-l-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-17-oxa- 4-azabicyclo [14.1.0] heptadecane-5,9-dione (Ixabepilone) Chloroform (45 ml) was added to (4S,7R,8S,9S,16S,Z)-4,8-dihydroxy-5,5,7,9,13- pentamethyl- 16-((E)- 1 -(2-methylthiazol-4-yl)prop- 1 -en-2-yl)azacyclohexadec- 13 -ene- 2,6-dione compound of formula G (0.43 gm) at 25-30°C under nitrogen atmosphere and stirred for 10 min at the same temperature. Cooled the reaction mixture to -15°C to -20°C and m-chloro perbenzoic acid (0.23 gm) was added and stirred for 4 hrs at the same temperature. Dichloromethane and 7percent aqueous sodium bicarbonate solution were added to the reaction mixture. Raised the temperature of the reaction mixture to 25-30°C and stirred for 15 min at the same temperature. Both the organic and aqueous layers were separated and the organic layer was washed with 7percent aqueous sodium bicarbonate solution, followed by with 25percent aqueous sodium sulfite solution and then finally with 5percent aqueous sodium chloride solution. Distilled off the solvent completely from the organic layer under reduced pressure. The obtained residue was purified by preparative HPLC to get the title compound. Yield: 0.31 gm; Purity by HPLC: 99.0percent.
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4369 - 4378
[2] Patent: US2014/256952, 2014, A1, . Location in patent: Paragraph 0288-0289; sheet 10; 20
[3] Patent: WO2015/87351, 2015, A2, . Location in patent: Page/Page column 60
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YieldReaction ConditionsOperation in experiment
3.2 g With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide; acetonitrile at 0 - 30℃; for 12 h; Inert atmosphere Example-52: Preparation of (lS,3S,7S,10R,HS,12S,16R)-7,ll-dihydroxy- 8,8,10,12,16-pentamethyl-3-[(lE)-l-methyl-2-(2-methyl-4-thiazolyl)ethenyI]-17-oxa- 4-azabicyclo[14.1.0]heptadecane-5,9-dione (Ixabepilone) A mixture of (3S,6R,7S,8S)-l l-((2R,3S)-3-((S,E)-2-amino-3-methyl-4-(2- methylthiazol-4-yl)but-3-enyl)-2-methyloxiran-2-yl)-3,7-dihydroxy-4,4,6,8-tetramethyl- 5-oxoundecanoic acid compound of formula K (3 gm) and dimethyl formamide (30 ml) was stirred for 10 min at 25-30°C under nitrogen atmosphere. Acetonitrile (480 ml) was added to the reaction mixture at 25-30°C. Cooled the reaction mixture to 0-5°C, 1- hydroxybenzotriazole (0.23 gm) and l-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.2 gm) were added. Raised the temperature of the reaction mixture to 25- 30°C and stirred for 12 hrs at the same temperature. Water and ethyl acetate were added to the reaction mixture at 25-30°C and stirred for 10 min at the same temperature. Both the organic and aqueous layers were separated and the aqueous layer was extracted with ethyl acetate. Combined the organic layers and washed with water followed by with aqueous sodium bicarbonate solution and then finally with aqueous sodium chloride solution. Distilled off the solvent completely from the organic layer under reduced pressure and then high vacuum was applied to get the title compound. Yield: 3.2 gm.
Reference: [1] Journal of the American Chemical Society, 2000, vol. 122, # 37, p. 8890 - 8897
[2] Patent: WO2015/87351, 2015, A2, . Location in patent: Page/Page column 62
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Reference: [1] Patent: WO2013/164102, 2013, A1, . Location in patent: Page/Page column 11
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[2] Patent: WO2015/87351, 2015, A2,
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[2] Patent: WO2015/87351, 2015, A2,
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