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

Base Information

Chemical Name:(3R,6R,8aS)-6-ethyl-6-{(E)-2-[3-(2-tert-butyldiphenylsilyloxyethyl)-1H-indol-2-yl]vinyl}-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one
CAS No.:1275592-89-6
Molecular Formula:C₄₃H₄₈N₂O₃Si
Molecular Weight:668.951
Hs Code.:

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

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Chemical Property of (3R,6R,8aS)-6-ethyl-6-{(E)-2-[3-(2-tert-butyldiphenylsilyloxyethyl)-1H-indol-2-yl]vinyl}-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one

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Technology Process of (3R,6R,8aS)-6-ethyl-6-{(E)-2-[3-(2-tert-butyldiphenylsilyloxyethyl)-1H-indol-2-yl]vinyl}-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one

There total 7 articles about (3R,6R,8aS)-6-ethyl-6-{(E)-2-[3-(2-tert-butyldiphenylsilyloxyethyl)-1H-indol-2-yl]vinyl}-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one 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: 65.0%

: 1275592-88-5
(3R,6R,8aS)-6-ethyl-3-phenyl-6-vinyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one

: 1275592-80-7
tert-butyl 3-(2-tert-butyldiphenylsiloxyethyl)-2-vinyl-1H-indole-1-carboxylate

: 1275592-89-6
(3R,6R,8aS)-6-ethyl-6-{(E)-2-[3-(2-tert-butyldiphenylsilyloxyethyl)-1H-indol-2-yl]vinyl}-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one

Guidance literature:: With Hoveyda-Grubbs catalyst second generation; In 5,5-dimethyl-1,3-cyclohexadiene; at 140 ℃; for 3h; Inert atmosphere;
DOI:10.1021/ol200320z

Reference yield:

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

: 1275592-89-6
(3R,6R,8aS)-6-ethyl-6-{(E)-2-[3-(2-tert-butyldiphenylsilyloxyethyl)-1H-indol-2-yl]vinyl}-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one

Guidance literature:: Multi-step reaction with 2 steps

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

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; Hoveyda-Grubbs catalyst second generation; trifuran-2-yl-phosphane; tetrabutyl-ammonium chloride; In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide; 1: Stille coupling;
DOI:10.1021/ol200320z

Reference yield:

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

: 1275592-89-6
(3R,6R,8aS)-6-ethyl-6-{(E)-2-[3-(2-tert-butyldiphenylsilyloxyethyl)-1H-indol-2-yl]vinyl}-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one

Guidance literature:: Multi-step reaction with 2 steps

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

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; Hoveyda-Grubbs catalyst second generation; trifuran-2-yl-phosphane; tetrabutyl-ammonium chloride; In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide; 1: Stille coupling;
DOI:10.1021/ol200320z