Name: Cabazitaxel
SKU: 183133-96-2

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Basic Information

Molecular Structure:
CAS No.:	183133-96-2
Name:	Cabazitaxel
Article Data:	24

Formula:	C₄₅H₅₇NO₁₄
Molecular Weight:	835.946
Synonyms:	Cabazitaxelum;Jevtana;RPR 116258A;TXD 258;Taxoid XRP6258;UNII-51F690397J;XRP6258;[2aR[2aalpha,4beta,4abeta,6beta,9alpha(2R,3S),11beta,12alpha,12aalpha,12balpha]]-12b-Acetoxy-9-[3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionyloxy]-12-(benzoyloxy)-11-hydroxy-4,6-dimethoxy-4a,8,13,13-tetramethyl-2a,3,4,4a,5,6,9,10,11,12,12a,12b-d;TAX-258;RPR-116258A;{((tertbutoxy)carbonyl)amino}-2-hydroxy-3-phenylpropanoate1-hydroxy-7beta,10beta-dimethoxy-9-oxo-5beta,20-epoxytax-11-ene-2alpha,4,13alpha-triyl 4-acetate 2-benzoate 13-((2R,3S)-3-;
EINECS:	680-632-7
Density:	1.31
Melting Point:	180 °C
Boiling Point:	870.7±65.0 °C(Predicted)
Appearance:	white powder
Safety:	24/25
PSA:	202.45000
LogP:	4.95870

Synthetic route

: 1380584-07-5
1-hydroxy-7β,10β-di-methoxy-9-oxo-5β,20-epoxytax-11-ene-2α,4,13α-triyl 4-acetate 2-benzoate 13-{(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-trethylsilyloxy-3-phenylpropanoate}

Conditions	Yield
With pyridine; hydrogen fluoride In acetonitrile at -8 - 0℃; for 23.5h;	97%
With pyridine; hydrogen fluoride In acetonitrile at -8 - 0℃; for 23.5h;	97%
With toluene-4-sulfonic acid In tetrahydrofuran; methanol at 0 - 5℃; for 1h;	90%

Conditions	Yield
With methanol at 20℃; for 2h;	96.1%

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; ethanol at -8 - 0℃; for 23.5h;	95%
With hydrogenchloride In tetrahydrofuran; ethanol at -8 - 0℃; for 23.5h;	95%

: (2α,5β,7β,10β,13α)-4-(acetyloxy)-13-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-[2-methoxy-2-prop-2-yl oxy]-3-phenylpropionyl}oxy)-1-hydroxy-7,10-dimethoxy-9-oxo-5,20-epoxy-11-ene-2-yl benzoate

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 20 - 25℃; for 3h;	90%

: 1354900-66-5
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxen-13α-yl (2R,4S,5S)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate

Conditions	Yield
With hydrogenchloride In ethanol at -5 - -2℃; Inert atmosphere;	89%
With hydrogenchloride; water In ethyl acetate at 0 - 5℃;

: (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl)oxy)-11-hydroxy-4,6-dimethoxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

Conditions	Yield
With potassium carbonate In dichloromethane; water at 20℃; for 4h;	85.7%
In methanol at 25 - 35℃; for 14h;	40 g

: 183133-95-1
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-7β,10β-dimethoxy-9-oxo-11-taxene-13α-yl (2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate

Conditions	Yield
With hydrogenchloride; water In methanol at 20℃;	83%
With hydrogenchloride In 2-methyltetrahydrofuran; methanol; water at 20℃; for 0.5h;	81%
With hydrogenchloride In ethanol at 0 - 5℃; Concentration; Inert atmosphere;
With hydrogenchloride In methanol; dichloromethane; water at 0℃; for 1h;

Conditions	Yield
With acetic acid In tetrahydrofuran; water at 50℃; for 4h; Inert atmosphere;	83%
With acetic acid In tetrahydrofuran; water at 50℃; for 4h; Inert atmosphere;	83%

: 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxen-13α-yl (2R,4S,5S)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate

Conditions	Yield
With hydrogenchloride In ethyl acetate at 0℃;	71%

: 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxen-13α-yl-(2S,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate