(1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-1-hydroxy-9,10-[(1S)-2-propenylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(tert-butoxycarbonylamino)-3-(5-trifluoromethyl-2-pyridyl)-2-triisopropylsilyloxypropionate

Base Information

• Chemical Name: (1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-1-hydroxy-9,10-[(1S)-2-propenylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(tert-butoxycarbonylamino)-3-(5-trifluoromethyl-2-pyridyl)-2-triisopropylsilyloxypropionate
• CAS No.: 647840-50-4
• Molecular Formula: C₅₅H₇₅F₃N₂O₁₃Si
• Molecular Weight: 1057.29
• Mol file: 647840-50-4.mol

Synonyms:(1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-1-hydroxy-9,10-[(1S)-2-propenylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(tert-butoxycarbonylamino)-3-(5-trifluoromethyl-2-pyridyl)-2-triisopropylsilyloxypropionate

Chemical Property of (1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-1-hydroxy-9,10-[(1S)-2-propenylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(tert-butoxycarbonylamino)-3-(5-trifluoromethyl-2-pyridyl)-2-triisopropylsilyloxypropionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-1-hydroxy-9,10-[(1S)-2-propenylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(tert-butoxycarbonylamino)-3-(5-trifluoromethyl-2-pyridyl)-2-triisopropylsilyloxypropionate

There total 8 articles about (1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-1-hydroxy-9,10-[(1S)-2-propenylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(tert-butoxycarbonylamino)-3-(5-trifluoromethyl-2-pyridyl)-2-triisopropylsilyloxypropionate 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%

(1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-(acetoxy)-2-(benzoyloxy)-1,13-dihydroxy-5,20-epoxy-9,10-[(1S)-2-propenylidenedioxy]tax-11-ene (333754-19-1) + (3R,4S)-1-(tert-butoxycarbonyl)-4-(5-trifluoromethyl-2-pyridyl)-3-triisopropylsilyloxy-2-azetidinone (647840-47-9) → (1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-1-hydroxy-9,10-[(1S)-2-propenylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(tert-butoxycarbonylamino)-3-(5-trifluoromethyl-2-pyridyl)-2-triisopropylsilyloxypropionate (647840-50-4)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; cooling;

DOI:10.1016/S0968-0896(03)00454-1

Reference yield:

5-(trifluoromethyl)pyridine-2-carbaldehyde (31224-82-5) → (1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-1-hydroxy-9,10-[(1S)-2-propenylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(tert-butoxycarbonylamino)-3-(5-trifluoromethyl-2-pyridyl)-2-triisopropylsilyloxypropionate (647840-50-4)

Guidance literature:

Multi-step reaction with 7 steps

1: Na₂SO₄ / benzene / 20 °C

2: triethylamine / CH₂Cl₂ / -78 - 20 °C

3: K₂CO₃ / methanol; tetrahydrofuran / 20 °C

4: imidazole / dimethylformamide / 20 °C

5: 33 percent / ceric ammonium nitrate / acetonitrile; H₂O / cooling

6: 99 percent / 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 20 °C

7: 92 percent / LiHMDS / tetrahydrofuran / cooling

With 1H-imidazole; dmap; ammonium cerium(IV) nitrate; potassium carbonate; sodium sulfate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene; 2: Staudinger reaction;

DOI:10.1016/S0968-0896(03)00454-1

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-1-hydroxy-9,10-[(1S)-2-propenylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(tert-butoxycarbonylamino)-3-(5-trifluoromethyl-2-pyridyl)-2-triisopropylsilyloxypropionate (647840-50-4)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / 20 °C

2: 33 percent / ceric ammonium nitrate / acetonitrile; H₂O / cooling

3: 99 percent / 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 20 °C

4: 92 percent / LiHMDS / tetrahydrofuran / cooling

With 1H-imidazole; dmap; ammonium cerium(IV) nitrate; lithium hexamethyldisilazane; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0968-0896(03)00454-1

upstream raw materials:

(1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-(acetoxy)-2-(benzoyloxy)-1,13-dihydroxy-5,20-epoxy-9,10-[(1S)-2-propenylidenedioxy]tax-11-ene

(3R,4S)-1-(tert-butoxycarbonyl)-4-(5-trifluoromethyl-2-pyridyl)-3-triisopropylsilyloxy-2-azetidinone

5-(trifluoromethyl)pyridine-2-carbaldehyde

triisopropylsilyl chloride

Downstream raw materials:

(1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-1-hydroxy-9,10-[(1S)-2-propenylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-(5-trifluoromethyl-2-pyridyl)propionate