(R)-2-{(4aR,12aS)-7-(2-tert-butyldiphenylsilyloxyethyl)-4a-ethyl-1,2,3,4,4a,5,6,12a-octahydroindolo[1,2-a][1,8]naphthyridin-1-yl}-2-phenylethanol

Base Information

Chemical Name:(R)-2-{(4aR,12aS)-7-(2-tert-butyldiphenylsilyloxyethyl)-4a-ethyl-1,2,3,4,4a,5,6,12a-octahydroindolo[1,2-a][1,8]naphthyridin-1-yl}-2-phenylethanol
CAS No.:1275592-91-0
Molecular Formula:C₄₃H₅₂N₂O₂Si
Molecular Weight:656.984
Hs Code.:

Synonyms:(R)-2-{(4aR,12aS)-7-(2-tert-butyldiphenylsilyloxyethyl)-4a-ethyl-1,2,3,4,4a,5,6,12a-octahydroindolo[1,2-a][1,8]naphthyridin-1-yl}-2-phenylethanol

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Chemical Property of (R)-2-{(4aR,12aS)-7-(2-tert-butyldiphenylsilyloxyethyl)-4a-ethyl-1,2,3,4,4a,5,6,12a-octahydroindolo[1,2-a][1,8]naphthyridin-1-yl}-2-phenylethanol

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Technology Process of (R)-2-{(4aR,12aS)-7-(2-tert-butyldiphenylsilyloxyethyl)-4a-ethyl-1,2,3,4,4a,5,6,12a-octahydroindolo[1,2-a][1,8]naphthyridin-1-yl}-2-phenylethanol

There total 10 articles about (R)-2-{(4aR,12aS)-7-(2-tert-butyldiphenylsilyloxyethyl)-4a-ethyl-1,2,3,4,4a,5,6,12a-octahydroindolo[1,2-a][1,8]naphthyridin-1-yl}-2-phenylethanol 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: 62.0%

: 1275592-90-9
(3R,6S,8aS)-6-{2-[3-(2-tert-butyldiphenylsilyloxyethyl)-1H-indol-2-yl]ethyl}-6-ethyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one

: 1275592-91-0
(R)-2-{(4aR,12aS)-7-(2-tert-butyldiphenylsilyloxyethyl)-4a-ethyl-1,2,3,4,4a,5,6,12a-octahydroindolo[1,2-a][1,8]naphthyridin-1-yl}-2-phenylethanol

Guidance literature:: (3R,6S,8aS)-6-{2-[3-(2-tert-butyldiphenylsilyloxyethyl)-1H-indol-2-yl]ethyl}-6-ethyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one; With sodium hydride; In diethyl ether; oil; at 0 ℃; for 0.5h; Inert atmosphere;

With diisobutylaluminium hydride; In diethyl ether; hexane; oil; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1021/ol200320z

Reference yield:

: 1275592-79-4
1-benzyloxy-6-tert-butyldiphenylsilyloxy-4-tributylstannylhexa-2,3-diene

: 1275592-91-0
(R)-2-{(4aR,12aS)-7-(2-tert-butyldiphenylsilyloxyethyl)-4a-ethyl-1,2,3,4,4a,5,6,12a-octahydroindolo[1,2-a][1,8]naphthyridin-1-yl}-2-phenylethanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: copper(l) iodide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; tetrabutyl-ammonium chloride / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

2.1: Hoveyda-Grubbs catalyst second generation / 5,5-dimethyl-1,3-cyclohexadiene / 3 h / 140 °C / Inert atmosphere

3.1: 5% Pd(II)/C(eggshell); hydrogen / ethyl acetate / 27 h / 20 °C / 760.05 Torr

4.1: sodium hydride / diethyl ether; oil / 0.5 h / 0 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; Hoveyda-Grubbs catalyst second generation; trifuran-2-yl-phosphane; 5% Pd(II)/C(eggshell); tetrabutyl-ammonium chloride; hydrogen; sodium hydride; In 5,5-dimethyl-1,3-cyclohexadiene; diethyl ether; ethyl acetate; N,N-dimethyl-formamide; oil; 1.1: Stille coupling;
DOI:10.1021/ol200320z

Reference yield:

: 161117-84-6
tert-butyl 2-iodophenylcarbamate

: 1275592-91-0
(R)-2-{(4aR,12aS)-7-(2-tert-butyldiphenylsilyloxyethyl)-4a-ethyl-1,2,3,4,4a,5,6,12a-octahydroindolo[1,2-a][1,8]naphthyridin-1-yl}-2-phenylethanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: copper(l) iodide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; tetrabutyl-ammonium chloride / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

2.1: Hoveyda-Grubbs catalyst second generation / 5,5-dimethyl-1,3-cyclohexadiene / 3 h / 140 °C / Inert atmosphere

3.1: 5% Pd(II)/C(eggshell); hydrogen / ethyl acetate / 27 h / 20 °C / 760.05 Torr

4.1: sodium hydride / diethyl ether; oil / 0.5 h / 0 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; Hoveyda-Grubbs catalyst second generation; trifuran-2-yl-phosphane; 5% Pd(II)/C(eggshell); tetrabutyl-ammonium chloride; hydrogen; sodium hydride; In 5,5-dimethyl-1,3-cyclohexadiene; diethyl ether; ethyl acetate; N,N-dimethyl-formamide; oil; 1.1: Stille coupling;
DOI:10.1021/ol200320z