Technology Process of (3R,3aR,7aR)-7-[(3S,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylethynyl]-3-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene
There total 15 articles about (3R,3aR,7aR)-7-[(3S,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylethynyl]-3-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene 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:
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![(3R,3aR,7aR)-7-[(3S,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylethynyl]-3-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene](/Databaselist/images/loading.webp)
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301153-96-8
(3R,3aR,7aR)-7-[(3S,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylethynyl]-3-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene
- Guidance literature:
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With
copper(l) iodide; bis(triphenylphosphine) palladium (Il) acetate; diethylamine;
In
N,N-dimethyl-formamide;
at 20 ℃;
for 1h;
DOI:10.1021/jo000443l
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301153-96-8
(3R,3aR,7aR)-7-[(3S,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylethynyl]-3-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene
- Guidance literature:
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Multi-step reaction with 15 steps
1: 100 percent / HCl / 6 h / 60 °C
2: 74 percent / Et3N / dimethylformamide / 16 h / 20 °C
3: 83 percent / CH2Cl2 / 120 h / 20 °C
4: 93 percent / Bu3SnH; AIBN / toluene / 2 h / 85 °C
5: 80 percent / pyridine; POCl3 / 10 h / 20 °C
6: 84 percent / TBAF / tetrahydrofuran / 15 h / 0 °C
7: 98 percent / pyridine / 1 h / 20 °C
8: 88 percent / aq. HCl / methanol / 2 h / 20 °C
9: 85 percent / diisopropyl azodicarboxylate; PPh3 / tetrahydrofuran / 2 h / 20 °C
10: 70 percent / NaOMe / methanol / 20 °C
11: 97 percent / imidazole / CH2Cl2 / 2 h / 20 °C
12: 96 percent / DIBAL-H / toluene / 2 h / -78 °C
13: 990 mg / PCC / CH2Cl2 / 2 h / 20 °C
14: 660 mg / n-BuLi / hexane; tetrahydrofuran / -78 - 20 °C
15: CuI; Pd(PPh3)2(OAc)2; Et2NH / dimethylformamide / 1 h / 20 °C
With
pyridine; 1H-imidazole; hydrogenchloride; copper(l) iodide; n-butyllithium; bis(triphenylphosphine) palladium (Il) acetate; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; diisobutylaluminium hydride; diethylamine; triethylamine; triphenylphosphine; pyridinium chlorochromate; trichlorophosphate;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
1: Methylation / 2: silylation / 3: thioacylation / 4: dethiocarboxylation / 5: Dehydration / 6: Dehydration / 7: Condensation / 8: Hydrolysis / 9: Esterification / 10: ester cleavage / 11: Condensation / 12: Reduction / 13: Oxidation / 14: Condensation / 15: Condensation;
DOI:10.1021/jo000443l
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301153-96-8
(3R,3aR,7aR)-7-[(3S,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylethynyl]-3-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene
- Guidance literature:
-
Multi-step reaction with 14 steps
1: 74 percent / Et3N / dimethylformamide / 16 h / 20 °C
2: 83 percent / CH2Cl2 / 120 h / 20 °C
3: 93 percent / Bu3SnH; AIBN / toluene / 2 h / 85 °C
4: 80 percent / pyridine; POCl3 / 10 h / 20 °C
5: 84 percent / TBAF / tetrahydrofuran / 15 h / 0 °C
6: 98 percent / pyridine / 1 h / 20 °C
7: 88 percent / aq. HCl / methanol / 2 h / 20 °C
8: 85 percent / diisopropyl azodicarboxylate; PPh3 / tetrahydrofuran / 2 h / 20 °C
9: 70 percent / NaOMe / methanol / 20 °C
10: 97 percent / imidazole / CH2Cl2 / 2 h / 20 °C
11: 96 percent / DIBAL-H / toluene / 2 h / -78 °C
12: 990 mg / PCC / CH2Cl2 / 2 h / 20 °C
13: 660 mg / n-BuLi / hexane; tetrahydrofuran / -78 - 20 °C
14: CuI; Pd(PPh3)2(OAc)2; Et2NH / dimethylformamide / 1 h / 20 °C
With
pyridine; 1H-imidazole; hydrogenchloride; copper(l) iodide; n-butyllithium; bis(triphenylphosphine) palladium (Il) acetate; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; diisobutylaluminium hydride; diethylamine; triethylamine; triphenylphosphine; pyridinium chlorochromate; trichlorophosphate;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
1: silylation / 2: thioacylation / 3: dethiocarboxylation / 4: Dehydration / 5: Dehydration / 6: Condensation / 7: Hydrolysis / 8: Esterification / 9: ester cleavage / 10: Condensation / 11: Reduction / 12: Oxidation / 13: Condensation / 14: Condensation;
DOI:10.1021/jo000443l
