(6Z,8S,8aS)-6-[(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene]-8-{[tert-butyl(dimethyl)silyl]oxy}-8-methyloctahydroindolizine

Base Information

Chemical Name:(6Z,8S,8aS)-6-[(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene]-8-{[tert-butyl(dimethyl)silyl]oxy}-8-methyloctahydroindolizine
CAS No.:251976-94-0
Molecular Formula:C₃₂H₅₃NO₂Si
Molecular Weight:511.864
Hs Code.:

Synonyms:(6Z,8S,8aS)-6-[(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene]-8-{[tert-butyl(dimethyl)silyl]oxy}-8-methyloctahydroindolizine

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Chemical Property of (6Z,8S,8aS)-6-[(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene]-8-{[tert-butyl(dimethyl)silyl]oxy}-8-methyloctahydroindolizine

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Technology Process of (6Z,8S,8aS)-6-[(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene]-8-{[tert-butyl(dimethyl)silyl]oxy}-8-methyloctahydroindolizine

There total 18 articles about (6Z,8S,8aS)-6-[(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene]-8-{[tert-butyl(dimethyl)silyl]oxy}-8-methyloctahydroindolizine 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: 60.0%

: 251976-93-9
benzyl (1S,2E)-1-ethyl-3-iodo-2-methyl-2-propenyl ether

: 251976-91-7
(6Z,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-6-[(2S)-3-iodo-2-methylpropylidene]-8-methyloctahydroindolizine

: 251976-94-0
(6Z,8S,8aS)-6-[(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene]-8-{[tert-butyl(dimethyl)silyl]oxy}-8-methyloctahydroindolizine

Guidance literature:: (6Z,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-6-[(2S)-3-iodo-2-methylpropylidene]-8-methyloctahydroindolizine; With tert.-butyl lithium; In diethyl ether; at -110 ℃;

With zinc(II) chloride; In tetrahydrofuran; at -78 - 0 ℃;

benzyl (1S,2E)-1-ethyl-3-iodo-2-methyl-2-propenyl ether; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In benzene;
DOI:10.1021/ja991918x

Reference yield:

: 251976-88-2
(6Z,8S,8aS)-6-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-8-methyloctahydro-8-indolizinol

: 251976-94-0
(6Z,8S,8aS)-6-[(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene]-8-{[tert-butyl(dimethyl)silyl]oxy}-8-methyloctahydroindolizine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 91 percent / 4-(dimethylamino)pyridine; 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 85 percent / tris(dimethylamino)sulfur (trimethylsilyl)difluoride / dimethylformamide / 7 h / 0 - 20 °C

3.1: 95 percent / triphenylphosphine; iodine; imidazole / CH₂Cl₂ / 8 h / 20 °C

4.1: t-BuLi / diethyl ether; pentane / 0.5 h / -110 °C

4.2: ZnCl₂ / diethyl ether; pentane; tetrahydrofuran / 2 h / -110 - 20 °C

4.3: 60 percent / Pd(PPh₃)4 / diethyl ether; pentane; various solvent(s) / 3 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; tris(dimethylamino)sulfonium trimethylsilyldifluoride; iodine; tert.-butyl lithium; triphenylphosphine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/jo0200466

Reference yield:

: 251976-87-1
(3Z,5S)-3-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-4-[(2S)-pyrrolidinyl]-1,4-pentanediol

: 251976-94-0
(6Z,8S,8aS)-6-[(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene]-8-{[tert-butyl(dimethyl)silyl]oxy}-8-methyloctahydroindolizine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 85 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 1 h / 20 °C

2.1: 91 percent / 4-(dimethylamino)pyridine; 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 85 percent / tris(dimethylamino)sulfur (trimethylsilyl)difluoride / dimethylformamide / 7 h / 0 - 20 °C

4.1: 95 percent / triphenylphosphine; iodine; imidazole / CH₂Cl₂ / 8 h / 20 °C

5.1: t-BuLi / diethyl ether; pentane / 0.5 h / -110 °C

5.2: ZnCl₂ / diethyl ether; pentane; tetrahydrofuran / 2 h / -110 - 20 °C

5.3: 60 percent / Pd(PPh₃)4 / diethyl ether; pentane; various solvent(s) / 3 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; carbon tetrabromide; tris(dimethylamino)sulfonium trimethylsilyldifluoride; iodine; tert.-butyl lithium; triphenylphosphine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/jo0200466