(8S,8aS)-8-hydroxy-8-methyl-(6Z)-<(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene>octahydroindolizidine

Base Information

• Chemical Name: (8S,8aS)-8-hydroxy-8-methyl-(6Z)-<(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene>octahydroindolizidine
• CAS No.: 98088-45-0
• Molecular Formula: C₂₆H₃₉NO₂
• Molecular Weight: 397.601
• Mol file: 98088-45-0.mol

Synonyms:(8S,8aS)-8-hydroxy-8-methyl-(6Z)-<(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene>octahydroindolizidine

Chemical Property of (8S,8aS)-8-hydroxy-8-methyl-(6Z)-<(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene>octahydroindolizidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8S,8aS)-8-hydroxy-8-methyl-(6Z)-<(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene>octahydroindolizidine

There total 44 articles about (8S,8aS)-8-hydroxy-8-methyl-(6Z)-<(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene>octahydroindolizidine 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: 88.0%

(6Z,8S,8aS)-6-[(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene]-8-{[tert-butyl(dimethyl)silyl]oxy}-8-methyloctahydroindolizine (251976-94-0) → (8S,8aS)-8-hydroxy-8-methyl-(6Z)-<(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene>octahydroindolizidine (98088-45-0)

Guidance literature:

With triethylamine tris(hydrogen fluoride); triethylamine; In acetonitrile; at 60 ℃; for 24h;

DOI:10.1021/jo0200466

Reference yield:

(3S)-3-(benzyloxy)-2-pentanone (98088-35-8) → (8S,8aS)-8-hydroxy-8-methyl-(6Z)-<(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene>octahydroindolizidine (98088-45-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 63 percent / CrCl₂ / tetrahydrofuran / 6 h / -10 - 20 °C

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

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

2.3: 60 percent / Pd(PPh₃)4 / diethyl ether; pentane; various solvent(s) / 3 h / 20 °C

3.1: 88 percent / triethylamine tris(hydrogenfluoride); triethylamine / acetonitrile / 24 h / 60 °C

With chromium dichloride; tert.-butyl lithium; triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; diethyl ether; acetonitrile; pentane;

DOI:10.1021/jo0200466

Reference yield:

(3Z,5S)-3-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-5-methyl-5-[(2S)-pyrrolidinyl]dihydro-2(3H)-furanone (444929-05-9) → (8S,8aS)-8-hydroxy-8-methyl-(6Z)-<(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene>octahydroindolizidine (98088-45-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: diisobutylaluminum hydride / toluene / 0.5 h / -30 °C

1.2: 71 percent / K₂CO₃ / toluene; H₂O / 1 h / 20 °C

2.1: 85 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 1 h / 20 °C

3.1: 91 percent / 4-(dimethylamino)pyridine; 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 85 percent / tris(dimethylamino)sulfur (trimethylsilyl)difluoride / dimethylformamide / 7 h / 0 - 20 °C

5.1: 95 percent / triphenylphosphine; iodine; imidazole / CH₂Cl₂ / 8 h / 20 °C

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

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

6.3: 60 percent / Pd(PPh₃)4 / diethyl ether; pentane; various solvent(s) / 3 h / 20 °C

7.1: 88 percent / triethylamine tris(hydrogenfluoride); triethylamine / acetonitrile / 24 h / 60 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; carbon tetrabromide; tris(dimethylamino)sulfonium trimethylsilyldifluoride; iodine; tert.-butyl lithium; diisobutylaluminium hydride; triethylamine tris(hydrogen fluoride); triethylamine; triphenylphosphine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; pentane;

DOI:10.1021/jo0200466

upstream raw materials:

(8S,8aS)-8-hydroxy-8-methyl-(6E)-<(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-1-iodo-4-octenylidene>octahydroindolizine

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

(S)-(-)-2-Benzyloxybutyraldehyde

(S)-2-(benzyloxy)butan-1-ol

Downstream raw materials:

(+)-pumiliotoxin A