(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-methoxy-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-methoxy-2-pyridyl)-2-triisopropylsilyloxypropionate
• CAS No.: 333754-21-5
• Molecular Formula: C₅₅H₇₈N₂O₁₄Si
• Molecular Weight: 1019.31
• Mol file: 333754-21-5.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-methoxy-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-methoxy-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-methoxy-2-pyridyl)-2-triisopropylsilyloxypropionate

There total 3 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-methoxy-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: 100.0%

(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)-4-(5-methoxy-2-pyridyl)-1-(tert-butoxycarbonyl)-3-triisopropylsilyloxy-2-azetidinone (333754-20-4) → (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-methoxy-2-pyridyl)-2-triisopropylsilyloxypropionate (333754-21-5)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; cooling;

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

Reference yield:

5-methoxy-2-pyridinecarboxaldehyde (22187-96-8) → (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-methoxy-2-pyridyl)-2-triisopropylsilyloxypropionate (333754-21-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 0 °C

1.2: (CH₃)3SiCl / tetrahydrofuran / 0 °C

2.1: lithium diisopropylamide / tetrahydrofuran; hexane / -78 °C

2.2: tetrahydrofuran; hexane / -78 - 20 °C

3.1: 91 percent / 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 20 °C

4.1: 100 percent / LiHMDS / tetrahydrofuran / cooling

With dmap; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; hexane;

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

Reference yield:

(3R,4S)-4-(5-methoxy-2-pyridyl)-3-triisopropylsilyloxy-2-azetidinone (647840-53-7) → (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-methoxy-2-pyridyl)-2-triisopropylsilyloxypropionate (333754-21-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 20 °C

2: 100 percent / LiHMDS / tetrahydrofuran / cooling

With dmap; 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)-1,13-dihydroxy-5,20-epoxy-9,10-[(1S)-2-propenylidenedioxy]tax-11-ene

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

5-methoxy-2-pyridinecarboxaldehyde

(3R,4S)-4-(5-methoxy-2-pyridyl)-3-triisopropylsilyloxy-2-azetidinone

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-methoxy-2-pyridyl)propionate