(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-2-((6-(((benzyloxy)carbonyl)amino)hexanoyl)oxy)-3-((tertbutoxycarbonyl)amino)-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

Base Information

• Chemical Name: (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-2-((6-(((benzyloxy)carbonyl)amino)hexanoyl)oxy)-3-((tertbutoxycarbonyl)amino)-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
• CAS No.: 1308398-77-7
• Molecular Formula: C₅₉H₇₄N₂O₁₇
• Molecular Weight: 1083.24
• Mol file: 1308398-77-7.mol

Synonyms:(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-2-((6-(((benzyloxy)carbonyl)amino)hexanoyl)oxy)-3-((tertbutoxycarbonyl)amino)-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

Chemical Property of (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-2-((6-(((benzyloxy)carbonyl)amino)hexanoyl)oxy)-3-((tertbutoxycarbonyl)amino)-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

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-2-((6-(((benzyloxy)carbonyl)amino)hexanoyl)oxy)-3-((tertbutoxycarbonyl)amino)-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

There total 2 articles about (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-2-((6-(((benzyloxy)carbonyl)amino)hexanoyl)oxy)-3-((tertbutoxycarbonyl)amino)-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 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

carbazitaxel (183133-96-2,1714967-27-7) + 6-(benzyloxycarbonylamino)hexanoic acid (1947-00-8) → (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-2-((6-(((benzyloxy)carbonyl)amino)hexanoyl)oxy)-3-((tertbutoxycarbonyl)amino)-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 (1308398-77-7)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;

DOI:10.1021/acs.jmedchem.9b00892

Reference yield:

6-(benzyloxycarbonylamino)hexanoic acid (1947-00-8) → (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-2-((6-(((benzyloxy)carbonyl)amino)hexanoyl)oxy)-3-((tertbutoxycarbonyl)amino)-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 (1308398-77-7)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at -5 - -2 ℃;

Reference yield: 65.0%

(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-2-((6-(((benzyloxy)carbonyl)amino)hexanoyl)oxy)-3-((tertbutoxycarbonyl)amino)-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 (1308398-77-7) → (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-2-((6-aminohexanoyl)oxy)-3-((tert-butoxycarbonyl)amino)-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

Guidance literature:

With methanesulfonic acid; palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; for 1h; under 1551.49 Torr;

DOI:10.1021/acs.jmedchem.9b00892

upstream raw materials:

carbazitaxel

6-(benzyloxycarbonylamino)hexanoic acid

Downstream raw materials:

cabazitaxel aminohexanoate