2-(2-Amino-phenyl)-1-((1S,2R,4aR,5S,6S,8aS)-2-hydroxymethyl-1,5,8a-trimethyl-6-triethylsilanyloxy-5-vinyl-decahydro-naphthalen-1-yl)-ethanone

Base Information

Chemical Name:2-(2-Amino-phenyl)-1-((1S,2R,4aR,5S,6S,8aS)-2-hydroxymethyl-1,5,8a-trimethyl-6-triethylsilanyloxy-5-vinyl-decahydro-naphthalen-1-yl)-ethanone
CAS No.:887138-32-1
Molecular Formula:C₃₀H₄₉NO₃Si
Molecular Weight:499.809
Hs Code.:

Synonyms:2-(2-Amino-phenyl)-1-((1S,2R,4aR,5S,6S,8aS)-2-hydroxymethyl-1,5,8a-trimethyl-6-triethylsilanyloxy-5-vinyl-decahydro-naphthalen-1-yl)-ethanone

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Chemical Property of 2-(2-Amino-phenyl)-1-((1S,2R,4aR,5S,6S,8aS)-2-hydroxymethyl-1,5,8a-trimethyl-6-triethylsilanyloxy-5-vinyl-decahydro-naphthalen-1-yl)-ethanone

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Technology Process of 2-(2-Amino-phenyl)-1-((1S,2R,4aR,5S,6S,8aS)-2-hydroxymethyl-1,5,8a-trimethyl-6-triethylsilanyloxy-5-vinyl-decahydro-naphthalen-1-yl)-ethanone

There total 7 articles about 2-(2-Amino-phenyl)-1-((1S,2R,4aR,5S,6S,8aS)-2-hydroxymethyl-1,5,8a-trimethyl-6-triethylsilanyloxy-5-vinyl-decahydro-naphthalen-1-yl)-ethanone 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: 85.0%

: 887138-24-1
(3aR,5aR,6S,7S,9aS,9bS)-6,9a,9b-Trimethyl-7-triethylsilanyloxy-6-vinyl-decahydro-naphtho[1,2-c]furan-1-one

: 82185-43-1
N-(trimethylsilyl)-o-toluidine

: 887138-32-1
2-(2-Amino-phenyl)-1-((1S,2R,4aR,5S,6S,8aS)-2-hydroxymethyl-1,5,8a-trimethyl-6-triethylsilanyloxy-5-vinyl-decahydro-naphthalen-1-yl)-ethanone

Guidance literature:: N-(trimethylsilyl)-o-toluidine; With sec.-butyllithium; In diethyl ether; hexane; cyclohexane; at -30 - 0 ℃;

(3aR,5aR,6S,7S,9aS,9bS)-6,9a,9b-Trimethyl-7-triethylsilanyloxy-6-vinyl-decahydro-naphtho[1,2-c]furan-1-one; In diethyl ether; hexane; cyclohexane; at -50 - 8 ℃; for 1.5h;
DOI:10.1021/ol060290+

Reference yield:

: 887138-29-6
(3aR,5aR,6R,7S,9aS,9bS)-7-Hydroxy-6-hydroxymethyl-6,9a,9b-trimethyl-decahydro-naphtho[1,2-c]furan-1-one

: 887138-32-1
2-(2-Amino-phenyl)-1-((1S,2R,4aR,5S,6S,8aS)-2-hydroxymethyl-1,5,8a-trimethyl-6-triethylsilanyloxy-5-vinyl-decahydro-naphthalen-1-yl)-ethanone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / 2,2,6,6-tetramethylpiperidine-1-oxyl; potassium bromide; NaHCO₃ / sodium hypochlorite / CH₂Cl₂; H₂O / 25 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1.08 h / 0 - 24 °C

3.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h / 0 - 24 °C

3.2: 95 percent / tetrahydrofuran; toluene / 0.5 h / 0 - 24 °C

4.1: sec-butyllithium / diethyl ether; hexane; cyclohexane / -30 - 0 °C

4.2: 184 mg / diethyl ether; hexane; cyclohexane / 1.5 h / -50 - 8 °C

With 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sec.-butyllithium; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium bromide; sodium hypochlorite; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; water; toluene; 3.2: Wittig reaction;
DOI:10.1021/jo062422i

Reference yield:

: 389103-79-1
(3aR,5aR,6R,7S,9aS,9bS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-6,9a,9b-trimethyl-decahydro-naphtho[1,2-c]furan-1-one

: 887138-32-1
2-(2-Amino-phenyl)-1-((1S,2R,4aR,5S,6S,8aS)-2-hydroxymethyl-1,5,8a-trimethyl-6-triethylsilanyloxy-5-vinyl-decahydro-naphthalen-1-yl)-ethanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 40 h / 24 °C

2.1: 100 percent / 2,2,6,6-tetramethylpiperidine-1-oxyl; potassium bromide; NaHCO₃ / sodium hypochlorite / CH₂Cl₂; H₂O / 25 °C

3.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1.08 h / 0 - 24 °C

4.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h / 0 - 24 °C

4.2: 95 percent / tetrahydrofuran; toluene / 0.5 h / 0 - 24 °C

5.1: sec-butyllithium / diethyl ether; hexane; cyclohexane / -30 - 0 °C

5.2: 184 mg / diethyl ether; hexane; cyclohexane / 1.5 h / -50 - 8 °C

With 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutyl ammonium fluoride; sec.-butyllithium; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium bromide; sodium hypochlorite; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; water; toluene; 4.2: Wittig reaction;
DOI:10.1021/jo062422i