(1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-1-hydroxy-9,10-[(1S)-2-(morpholino)ethylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(5-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-(morpholino)ethylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(5-benzyloxy-2-pyridyl)-3-(tert-butoxycarbonylamino)-2-hydroxypropionate
CAS No.:647840-16-2
Molecular Formula:C₅₅H₆₉N₃O₁₅
Molecular Weight:1012.16
Hs Code.:

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

There total 14 articles about (1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-1-hydroxy-9,10-[(1S)-2-(morpholino)ethylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(5-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:

: 110-91-8,99108-56-2
morpholine

: C₅₁H₆₀N₂O₁₅

: 647840-16-2
(1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-1-hydroxy-9,10-[(1S)-2-(morpholino)ethylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(5-benzyloxy-2-pyridyl)-3-(tert-butoxycarbonylamino)-2-hydroxypropionate

Guidance literature:: With sodium cyanoborohydride; acetic acid; In ethanol; at 20 ℃; for 0.25h;
DOI:10.1016/S0968-0896(03)00454-1

Reference yield:

: 1121-78-4
5-Hydroxy-2-methylpyridine

: 647840-16-2
(1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-1-hydroxy-9,10-[(1S)-2-(morpholino)ethylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(5-benzyloxy-2-pyridyl)-3-(tert-butoxycarbonylamino)-2-hydroxypropionate

Guidance literature:: Multi-step reaction with 13 steps

1.1: 82 percent / NaH / tetrahydrofuran; dimethylformamide / 20 °C

2.1: 96 percent / meta-chloroperoxybenzoic acid / CHCl₃ / 1 h / cooling

3.1: 77 percent / 0.5 h / 130 °C

4.1: 75 percent / NaOH / ethanol; H₂O / 1.5 h / Heating

5.1: 77 percent / MnO₂ / CHCl₃ / 0.08 h / Heating

6.1: tetrahydrofuran / 0.5 h / 0 °C

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

7.1: lithium diisopropylamide / tetrahydrofuran; hexane / 2 h / -78 °C

7.2: 780 mg / tetrahydrofuran; hexane / -78 - 20 °C

8.1: 88 percent / 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 1 h / 20 °C

9.1: 82 percent / LiHMDS / tetrahydrofuran / 0.5 h / cooling

10.1: 100 percent / Bu₄NF / tetrahydrofuran / 0.25 h / cooling

11.1: OsO₄; N-methylmorpholine N-oxide / tetrahydrofuran; H₂O; acetone / 2.5 h / 20 °C

12.1: NaIO₄ / tetrahydrofuran; methanol; H₂O / 0.5 h / 20 °C

13.1: 82 mg / NaBH₃CN; acetic acid / ethanol / 0.25 h / 20 °C

With dmap; manganese(IV) oxide; sodium hydroxide; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; sodium hydride; sodium cyanoborohydride; acetic acid; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; hexane; chloroform; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0968-0896(03)00454-1

Reference yield:

: 63793-98-6
5-benzyloxy-2-methyl-pyridine

: 647840-16-2
(1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-1-hydroxy-9,10-[(1S)-2-(morpholino)ethylidenedioxy]tax-11-en-13-yl (2R,3S)-3-(5-benzyloxy-2-pyridyl)-3-(tert-butoxycarbonylamino)-2-hydroxypropionate

Guidance literature:: Multi-step reaction with 12 steps

1.1: 96 percent / meta-chloroperoxybenzoic acid / CHCl₃ / 1 h / cooling

2.1: 77 percent / 0.5 h / 130 °C

3.1: 75 percent / NaOH / ethanol; H₂O / 1.5 h / Heating

4.1: 77 percent / MnO₂ / CHCl₃ / 0.08 h / Heating

5.1: tetrahydrofuran / 0.5 h / 0 °C

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

6.1: lithium diisopropylamide / tetrahydrofuran; hexane / 2 h / -78 °C

6.2: 780 mg / tetrahydrofuran; hexane / -78 - 20 °C

7.1: 88 percent / 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 1 h / 20 °C

8.1: 82 percent / LiHMDS / tetrahydrofuran / 0.5 h / cooling

9.1: 100 percent / Bu₄NF / tetrahydrofuran / 0.25 h / cooling

10.1: OsO₄; N-methylmorpholine N-oxide / tetrahydrofuran; H₂O; acetone / 2.5 h / 20 °C

11.1: NaIO₄ / tetrahydrofuran; methanol; H₂O / 0.5 h / 20 °C

12.1: 82 mg / NaBH₃CN; acetic acid / ethanol / 0.25 h / 20 °C

With dmap; manganese(IV) oxide; sodium hydroxide; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; sodium cyanoborohydride; acetic acid; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; hexane; chloroform; water; acetone;
DOI:10.1016/S0968-0896(03)00454-1