(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-(3-benzyloxy-2-pyridyl)-3-(tert-butoxycarbonylamino)-2-hydroxypropionate

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-(3-benzyloxy-2-pyridyl)-3-(tert-butoxycarbonylamino)-2-hydroxypropionate
CAS No.:647840-34-4
Molecular Formula:C₅₂H₆₂N₂O₁₄
Molecular Weight:939.069
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-(3-benzyloxy-2-pyridyl)-3-(tert-butoxycarbonylamino)-2-hydroxypropionate

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-(3-benzyloxy-2-pyridyl)-3-(tert-butoxycarbonylamino)-2-hydroxypropionate

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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-(3-benzyloxy-2-pyridyl)-3-(tert-butoxycarbonylamino)-2-hydroxypropionate

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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-(3-benzyloxy-2-pyridyl)-3-(tert-butoxycarbonylamino)-2-hydroxypropionate

There total 4 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-(3-benzyloxy-2-pyridyl)-3-(tert-butoxycarbonylamino)-2-hydroxypropionate 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%

: 647840-33-3
(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-(3-benzyloxy-2-pyridyl)-3-(tert-butoxycarbonylamino)-2-triisopropylsilyloxypropionate

: 647840-34-4
(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-(3-benzyloxy-2-pyridyl)-3-(tert-butoxycarbonylamino)-2-hydroxypropionate

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

Reference yield:

: 14173-30-9
3-hydroxy-2-hydroxymethylpyridine hydrochloride

: 647840-34-4
(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-(3-benzyloxy-2-pyridyl)-3-(tert-butoxycarbonylamino)-2-hydroxypropionate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 66 percent / KOH / ethanol / 24 h / Heating

2.1: 73 percent / MnO₂ / CHCl₃ / 1.33 h / Heating

3.1: tetrahydrofuran / 0.5 h / 0 °C

3.2: (CH₃)3SiCl / tetrahydrofuran / 0.5 h / 0 °C

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

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

5.1: 83 percent / 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 20 °C

6.1: 90 percent / LiHMDS / tetrahydrofuran / cooling

7.1: 94 percent / Bu₄NF / tetrahydrofuran / cooling

With dmap; manganese(IV) oxide; potassium hydroxide; tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; ethanol; hexane; chloroform;
DOI:10.1016/S0968-0896(03)00454-1

Reference yield:

: 94454-57-6
3-(phenylmethoxy)-2-pyridinecarboxaldehyde

: 647840-34-4
(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-(3-benzyloxy-2-pyridyl)-3-(tert-butoxycarbonylamino)-2-hydroxypropionate

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrahydrofuran / 0.5 h / 0 °C

1.2: (CH₃)3SiCl / tetrahydrofuran / 0.5 h / 0 °C

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

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

3.1: 83 percent / 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 20 °C

4.1: 90 percent / LiHMDS / tetrahydrofuran / cooling

5.1: 94 percent / Bu₄NF / tetrahydrofuran / cooling

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