(3S,6R,8aR)-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

Base Information

Chemical Name:(3S,6R,8aR)-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
CAS No.:1275592-96-5
Molecular Formula:C₄₃H₅₀N₂O₃Si
Molecular Weight:670.967
Hs Code.:

Synonyms:(3S,6R,8aR)-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

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Chemical Property of (3S,6R,8aR)-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

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Technology Process of (3S,6R,8aR)-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

There total 9 articles about (3S,6R,8aR)-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 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:

: 1275592-95-4
(3S,6S,8aR)-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

: 1275592-96-5
(3S,6R,8aR)-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

Guidance literature:: With 5% Pd(II)/C(eggshell); hydrogen; In ethyl acetate; at 20 ℃; for 27h; under 760.051 Torr;
DOI:10.1021/ol200320z

Reference yield:

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

: 1275592-96-5
(3S,6R,8aR)-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

Guidance literature:: Multi-step reaction with 3 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

3: 5% Pd(II)/C(eggshell); hydrogen / ethyl acetate / 27 h / 20 °C / 760.05 Torr

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; In 5,5-dimethyl-1,3-cyclohexadiene; ethyl acetate; N,N-dimethyl-formamide; 1: Stille coupling;
DOI:10.1021/ol200320z

Reference yield:

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

: 1275592-96-5
(3S,6R,8aR)-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

Guidance literature:: Multi-step reaction with 3 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

3: 5% Pd(II)/C(eggshell); hydrogen / ethyl acetate / 27 h / 20 °C / 760.05 Torr

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; In 5,5-dimethyl-1,3-cyclohexadiene; ethyl acetate; N,N-dimethyl-formamide; 1: Stille coupling;
DOI:10.1021/ol200320z