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[ CAS No. 188062-50-2 ] {[proInfo.proName]}

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Chemical Structure| 188062-50-2
Chemical Structure| 188062-50-2
Structure of 188062-50-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 188062-50-2 ]

CAS No. :188062-50-2 MDL No. :MFCD04112763
Formula : C28H38N12O6S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 670.74 Pubchem ID :-
Synonyms :
ABC sulfate;Abacavir Hemisulfate;1592U89

Calculated chemistry of [ 188062-50-2 ]

Physicochemical Properties

Num. heavy atoms : 47
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.5
Num. rotatable bonds : 8
Num. H-bond acceptors : 12.0
Num. H-bond donors : 8.0
Molar Refractivity : 175.03
TPSA : 286.74 Ų

Pharmacokinetics

GI absorption : Low
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) : -10.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.62
Log Po/w (XLOGP3) : 0.36
Log Po/w (WLOGP) : 2.12
Log Po/w (MLOGP) : -0.46
Log Po/w (SILICOS-IT) : -0.27
Consensus Log Po/w : 1.07

Druglikeness

Lipinski : 3.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 5.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -3.98
Solubility : 0.0701 mg/ml ; 0.000105 mol/l
Class : Soluble
Log S (Ali) : -5.95
Solubility : 0.000759 mg/ml ; 0.00000113 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -1.92
Solubility : 8.12 mg/ml ; 0.0121 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 5.91

Safety of [ 188062-50-2 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P280-P305+P351+P338 UN#:2811
Hazard Statements:H317-H319-H341-H350-H360 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 188062-50-2 ]

* 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.

  • Downstream synthetic route of [ 188062-50-2 ]

[ 188062-50-2 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 136470-78-5 ]
  • abacavir sulfate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid In ethyl acetate at 20℃; for 3h; 1 Example 1 Abacavir free base (3.0 gm, obtained by the process described in example 21 of US 5,034, 394) is dissolved in ethyl acetate (15 ml) and conc. sulfuric acid (0.3 ml) is added to the solution. Then the contents are stirred for 3 hours at 20°C and filtered to give 3.0 gm of form I abacavir sulfate.
With sulfuric acid In methanol; di-isopropyl ether at 0 - 25℃; for 2h; 5 Example 5 Abacavir free base (3.0 gm) is dissolved in methanol (15 ml) and sulfuric acid (0.3 ml) is added to the solution. The contents then are cooled to 0°C and diisopropyl ether (15 ml) is added. The reaction mass is stirred for 2 hours at about 25°C and the separated solid is filtered to give 3.0 gm of form III abacavir sulfate.
With sulfuric acid In acetonitrile at 25℃; for 2h; 3 Example 3 Abacavir free base (3.0 gm) is dissolved in acetonitrile (15 ml) and sulfuric acid (0.3 ml) is added to the solution. Then the contents are stirred for 2 hours at 25°C and the separated solid is filtered to give 3.0 gm of form 11 abacavir sulfate.
With sulfuric acid In tert-butyl methyl ether at 25℃; for 1h; 4 Example 4 Abacavir free base (3.0 gm) is dissolved in methyl tert-butyl ether (25 ml) and sulfuric acid (0.3 ml) is added to the solution. Then the contents are stirred for 1 hours at 25°C and the separated solid is filtered to give 3.0 gm of form 11 abacavir sulfate.
With sulfuric acid In acetone at 25℃; for 6h; 2 Example 2 Abacavir free base (3.0 gm) is dissolved in acetone (20 ml) and CONC. sulfuric acid (0.3 ml) is added to the solution. Then the contents are stirred for 6 hours at 25°C and filtered to give 2.8 gm of form I abacavir sulfate.

  • 2
  • {(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol sulphate [ No CAS ]
  • [ 136470-78-5 ]
YieldReaction ConditionsOperation in experiment
78% With sodium hydroxide In water; ethyl acetate at 25 - 45℃; 2 EXAMPLE-2 PREPARATION OF (1S,4R)-4-[2-AMINO-(6-CYCLOPROPYLAMINO)-9H-PURIN-9- YL]-2-CYCLOPENTENE-1-METHANOL (ABACAVIR BASE) Abacavir hemisulfate (300 g, 0.453 mol) was suspended in mixture of ethyl acetate (3000 ml) and DM water (900 ml) at 25-30°C. The contents were heated to 40-45°C and pH of the suspension was adjusted to 6.0-6.1 with 20% w/w aqueous sodium hydroxide solution (-250 ml). Thereafter, organic layer was separated and aqueous layer was re-extracted with ethyl acetate (1 x 600 ml) at 40-45°C. Carbon enoanticromos (15 g) was added to the combined organic layer and contents were stirred for ∼1 h at 40-45°C. Carbon was removed through hyflo and residue was washed with pre-heated ethyl acetate (2 x 100 m1,40-45°C), Concentrated the filtrate at 50-60°C under reduced pressure (150-50 mm Hg) to obtain a foamy oily mass. Thereafter, acetone (1000 ml) was added to the concentrated mass and stirred for ∼30 min at 0-5°C. Product was filtered, washed with acetone (2 x 100 ml) under nitrogen atmosphere and dried at 40-50°C under reduced pressure (10-50 mm Hg) to a constant weight. Yield: 200 g (78% of Theory) Chromatographic Purity (by HPLC) : 99.86% Chiral Purity (by HPLC) :99.93% Assay (by HPLC, % w/w) : 99.4
  • 3
  • [ 136470-78-5 ]
  • {(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol sulphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With sulfuric acid In water; isopropyl alcohol at 50 - 55℃; for 2h; 18 Example 18: Preparation of {(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol sulphate To a solution of isopropyl alcohol and water was added {(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol (0.3492 mol). Heated to 50-55° C. Activated carbon was added and filtered through hyflo bed. To the filter MLs conc. Sulphuric acid (0.2 mol) was added drop wise at 50-55° C. Maintained the reaction mass for 2 hrs at the same temperature and allowed to cool to temperature. Stirred for about 2 hrs at room temperature, filtered and washed with chilled isopropyl alcohol to obtain pure Abacavir sulphate. The compound was confirmed by 1H-NMR, Mass, IR, SOR and XRD. (Yield: 95%, HPLC: >99.8%).
  • 4
  • [ 188062-50-2 ]
  • [ 136470-88-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine; 1H-imidazole / ethyl acetate / 20 h / 20 °C 2: pyridine / 1 h / 20 °C / Cooling with ice 3: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 20 °C / Cooling with ice
  • 5
  • [ 188062-50-2 ]
  • [ 2196216-60-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: pyridine; 1H-imidazole / ethyl acetate / 20 h / 20 °C 2: pyridine / 1 h / 20 °C / Cooling with ice 3: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 20 °C / Cooling with ice 4: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.5 h / 20 °C
  • 6
  • [ 188062-50-2 ]
  • [ 18162-48-6 ]
  • [ 1446418-44-5 ]
YieldReaction ConditionsOperation in experiment
93% With pyridine; 1H-imidazole In ethyl acetate at 20℃; for 20h; 4.2.1. Synthesis of 51-O-TBS-abacavir (5) Abacavir hemisulfate (332 mg, 990 mol) and imidazole (167 mg, 2.45 mmol) were coevaporatedwith anhydrous pyridine three times, and then suspended in anhydrous pyridine (8 mL). To themixture, tert-butyldimethylsilyl chloride (190 mg, 1.26 mmol) was added. The reaction mixture wasdiluted with ethyl acetate (100 mL) after continuous stirring for 20 h at room temperature, and theorganic layer was washed with saturated NaHCO3 (80 mL x 2) and brine (80 mL x 1), and then wasdried over Na2SO4. The solvent was evaporated in vacuo. The residue was co-evaporated with toluenethree times, and the product was purified with silica gel column chromatography with a stepwisegradient of 0%-2% methanol in chloroform. The fractions containing the product were evaporated togive a white foamy solid. Yield 367 mg (916 mol, 93%). TLC (CHCl3/MeOH, 10:1) Rf 0.54. 1H-NMR(500 MHz, CDCl3) δ (ppm) 7.54 (s, 1H), 6.11 (dt, J = 5.5 and 2 Hz, 1H), 5.83 (dt, J = 6 and 2.2 Hz, 1H),5.63 (m, 1H), 5.55 (tt, J = 5 and 2.2 Hz, 1H), 4.71 (br, 2H), 3.68 (dd, J = 10 and 5.8 Hz, 1H), 3.60 (dd, J = 10and 5.8 Hz, 1H), 2.99 (m, 2H), 2.74 (dt, J = 13.5 and 8.8 Hz, 1H), 0.89 (s, 9H), 0.86 (m, 2H), 0.61 (m, 2H),0.05 (s, 6H). FAB-HRMS m/z 401.2487 ([M + H]+, m/z 401.2485 calcd for C20H33ON6Si) (See Figure S5).
  • 7
  • [ 188062-50-2 ]
  • [ 18162-48-6 ]
  • [ 2185850-28-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine; 1H-imidazole / ethyl acetate / 20 h / 20 °C 2: pyridine / 1 h / 20 °C / Cooling with ice
  • 8
  • [ 188062-50-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere; Molecular sieve
  • 9
  • [ 188062-50-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere; Molecular sieve
  • 10
  • abacavir sulfate [ No CAS ]
  • [ 2906-60-7 ]
  • C22H30N6O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
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