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CAS No.: | 183133-94-0 |
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Name: | (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(Acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-9,11-dihydroxy-4,6-dimethoxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one |
Article Data: | 20 |
Molecular Structure: | |
Formula: | C31H40O10 |
Molecular Weight: | 572.653 |
Synonyms: | 7,10-MeO-10-DAB;7,10-Dimethoxy-10-DABIII; |
EINECS: | 1592732-453-0 |
Density: | 1.31 |
Boiling Point: | 675.8±55.0 °C(Predicted) |
PSA: | 137.82000 |
LogP: | 2.39000 |
10-deacetylbaccatin III
carbonic acid dimethyl ester
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene
Conditions | Yield |
---|---|
With dmap; caesium bromide; sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at -30℃; for 3h; Temperature; Reagent/catalyst; | 89.6% |
10-deacetylbaccatin III
methyl trifluoromethanesulfonate
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene
Conditions | Yield |
---|---|
Stage #1: 10-deacetylbaccatin III With lithium hexamethyldisilazane In tetrahydrofuran at -72℃; for 0.666667h; Inert atmosphere; Stage #2: methyl trifluoromethanesulfonate In tetrahydrofuran at -72℃; for 4.08333h; Inert atmosphere; | 87% |
Stage #1: 10-deacetylbaccatin III With n-butyllithium In tetrahydrofuran at -78 - -35℃; for 1h; Inert atmosphere; Stage #2: methyl trifluoromethanesulfonate In tetrahydrofuran for 1h; Temperature; | 55% |
7,10-methylthiomethyl-10-deacetylbaccatin III
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene
Conditions | Yield |
---|---|
With water; Raney nickel In methanol at 23℃; | 61% |
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-10β-methoxy-9-oxo-1β,13α,7β-trihydroxy-11-taxene
methyl iodide
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene
Conditions | Yield |
---|---|
With potassium hydride In tetrahydrofuran at 0 - 20℃; | 61% |
With sodium hydride In N,N-dimethyl acetamide at -15 - -5℃; for 1h; Concentration; | 58.8% |
With sodium hydride In N,N-dimethyl acetamide at -15 - -10℃; Time; | 58.8% |
Stage #1: 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-10β-methoxy-9-oxo-1β,13α,7β-trihydroxy-11-taxene; methyl iodide In N,N-dimethyl-formamide at 20 - 30℃; for 0.5h; Stage #2: With sodium hydride In N,N-dimethyl-formamide; paraffin oil at 0 - 5℃; Reagent/catalyst; Solvent; Temperature; |
13-acetyl-7,10-dimethoxy-10-DAB
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene
Conditions | Yield |
---|---|
With hydrazine hydrate In N,N-dimethyl-formamide at 23℃; for 18h; Inert atmosphere; | 53% |
10-deacetylbaccatin III
methyl iodide
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene
Conditions | Yield |
---|---|
Stage #1: 10-deacetylbaccatin III With n-butyllithium In tetrahydrofuran at -75 - -35℃; for 1h; Inert atmosphere; Stage #2: methyl iodide for 1h; | 52% |
With potassium hydride In tetrahydrofuran at -20 - 20℃; for 8h; | |
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 25℃; for 7.5h; Reagent/catalyst; Temperature; Solvent; Time; | |
With caesium bromide; sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at -20 - 20℃; for 2.33333h; Inert atmosphere; | |
With sodium hydride In N,N-dimethyl-formamide for 1.5h; Solvent; Temperature; | 10 g |
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,10β-dihydroxy-9-oxo-7β,13α-di(triethylsilyloxy)-11-taxene
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium hydride / tetrahydrofuran / -5 - 0 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 5 °C / Inert atmosphere 3: sodium hydride / tetrahydrofuran / -5 - 0 °C 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 5 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1: sodium hydride / tetrahydrofuran / -5 - 0 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 5 °C / Inert atmosphere 3: sodium hydride / -5 - 0 °C 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 5 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine tris(hydrogen fluoride) / dichloromethane / 16 h / 20 °C 2: potassium tert-butylate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C View Scheme |
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-9-oxo-10β-methoxy-7β,13α-di(triethylsilyloxy)-11-taxene
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 5 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / -5 - 0 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 5 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 5 °C / Inert atmosphere 2: sodium hydride / -5 - 0 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 5 °C / Inert atmosphere View Scheme |
7,10-di-O-1,3-dithian-2-yl-10-DAB
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene
Conditions | Yield |
---|---|
With hydrogen In N,N-dimethyl-formamide at 50℃; under 8274.59 Torr; for 23h; |
10-O-methyl-7-O-1,3-benzodithiolan-2-yl-10-DAB
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene
Conditions | Yield |
---|---|
With hydrogen In N,N-dimethyl-formamide at 20℃; under 2584.17 Torr; for 15h; |
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10-Deacetyl-7,10-dimethoxy-Baccatin III is an intermediate used to prepare Cabazitaxel.