(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

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-methoxy-2-pyridyl)propionate
CAS No.:333754-22-6
Molecular Formula:C₄₆H₅₈N₂O₁₄
Molecular Weight:862.972
Hs Code.:

(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

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-methoxy-2-pyridyl)propionate

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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-methoxy-2-pyridyl)propionate

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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-methoxy-2-pyridyl)propionate

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)-2-hydroxy-3-(5-methoxy-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: 91.0%

: 333754-21-5
(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-methoxy-2-pyridyl)-2-triisopropylsilyloxypropionate

: 333754-22-6
(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-methoxy-2-pyridyl)propionate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; cooling;
DOI:10.1016/S0968-0896(03)00454-1

Reference yield:

: 22187-96-8
5-methoxy-2-pyridinecarboxaldehyde

: 333754-22-6
(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-methoxy-2-pyridyl)propionate

Guidance literature:: Multi-step reaction with 5 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

5.1: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / cooling

With dmap; tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; hexane;
DOI:10.1016/S0968-0896(03)00454-1

Reference yield:

: 647840-53-7
(3R,4S)-4-(5-methoxy-2-pyridyl)-3-triisopropylsilyloxy-2-azetidinone

: 333754-22-6
(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-methoxy-2-pyridyl)propionate

Guidance literature:: Multi-step reaction with 3 steps

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

2: 100 percent / LiHMDS / tetrahydrofuran / cooling

3: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / cooling

With dmap; tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran;
DOI:10.1016/S0968-0896(03)00454-1