(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-methyl-2-pyridyl)propionate

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)-2-hydroxy-3-(5-methyl-2-pyridyl)propionate
• CAS No.: 647840-29-7
• Molecular Formula: C₄₆H₅₈N₂O₁₃
• Molecular Weight: 846.972
• Mol file: 647840-29-7.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)-2-hydroxy-3-(5-methyl-2-pyridyl)propionate

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)-2-hydroxy-3-(5-methyl-2-pyridyl)propionate

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)-2-hydroxy-3-(5-methyl-2-pyridyl)propionate

There total 7 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)-2-hydroxy-3-(5-methyl-2-pyridyl)propionate 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: 94.0%

(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-methyl-2-pyridyl)-2-triisopropylsilyloxypropionate (647840-28-6) → (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-methyl-2-pyridyl)propionate (647840-29-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; cooling;

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

Reference yield:

5-methylpicolinaldehyde (4985-92-6) → (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-methyl-2-pyridyl)propionate (647840-29-7)

Guidance literature:

Multi-step reaction with 8 steps

1: Na₂SO₄ / benzene / 1 h / 20 °C

2: 1.5 g / triethylamine / CH₂Cl₂ / -78 - 20 °C

3: K₂CO₃ / methanol; tetrahydrofuran / 1 h / 20 °C

4: 1.65 g / imidazole / dimethylformamide / 14 h / 20 °C

5: 27 percent / ceric ammonium nitrate / acetonitrile; H₂O / 1.5 h / cooling

6: 96 percent / 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 20 °C

7: 80 percent / LiHMDS / tetrahydrofuran / cooling

8: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / cooling

With 1H-imidazole; dmap; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; 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:

(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) → (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-methyl-2-pyridyl)propionate (647840-29-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / LiHMDS / tetrahydrofuran / cooling

2: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / cooling

With tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran;

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

upstream 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)-3-(5-methyl-2-pyridyl)-2-triisopropylsilyloxypropionate

5-methylpicolinaldehyde

(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)-4-(5-methyl-2-pyridyl)-3-triisopropylsilyloxy-2-azetidinone