Technology Process of (1R,3R)-5-[(1R,3aR,7aR)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-ylethynyl]-cyclohex-4-ene-1,3-diol
There total 10 articles about (1R,3R)-5-[(1R,3aR,7aR)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-ylethynyl]-cyclohex-4-ene-1,3-diol which
guide to synthetic route it.
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synthetic route:
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262594-20-7
(1R,3R)-5-[(1R,3aR,7aR)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-ylethynyl]-cyclohex-4-ene-1,3-diol
- Guidance literature:
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3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynylcyclohex-1-ene; 25-trimethylsilyloxy-de-A,B-cholest-8-en-8-yl trifluoromethanesulfonate;
With
copper(l) iodide; bis(triphenylphosphine) palladium (Il) acetate; diethylamine;
In
N,N-dimethyl-formamide;
With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
DOI:10.1016/S0040-4039(99)02152-8
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262594-20-7
(1R,3R)-5-[(1R,3aR,7aR)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-ylethynyl]-cyclohex-4-ene-1,3-diol
- Guidance literature:
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Multi-step reaction with 10 steps
1.1: 57 percent
2.1: 80 percent / POCl3; pyridine
3.1: 84 percent / TBAF / tetrahydrofuran
4.1: 98 percent / PPh3; DIAD / tetrahydrofuran
5.1: 83 percent / MeONa / methanol
6.1: 95 percent / imidazole / CH2Cl2
7.1: 96 percent / DIBAL-H / toluene
8.1: 98 percent / PCC / CH2Cl2
9.1: 70 percent / BuLi / tetrahydrofuran
10.1: Pd(PPh3)2(OAc)2*CuI; Et2NH / dimethylformamide
10.2: 85 percent / TBAF / tetrahydrofuran
With
pyridine; 1H-imidazole; copper(l) iodide; n-butyllithium; bis(triphenylphosphine) palladium (Il) acetate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; sodium methylate; diisobutylaluminium hydride; diethylamine; triphenylphosphine; pyridinium chlorochromate; trichlorophosphate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
2.1: Dehydration / 3.1: Hydrolysis / 4.1: Acylation / 5.1: deprotection / 6.1: Etherification / 7.1: Reduction / 8.1: Oxidation / 9.1: Condensation / 10.1: Condensation / 10.2: deprotection;
DOI:10.1016/S0040-4039(99)02152-8
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262594-20-7
(1R,3R)-5-[(1R,3aR,7aR)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-ylethynyl]-cyclohex-4-ene-1,3-diol
- Guidance literature:
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Multi-step reaction with 9 steps
1.1: 80 percent / POCl3; pyridine
2.1: 84 percent / TBAF / tetrahydrofuran
3.1: 98 percent / PPh3; DIAD / tetrahydrofuran
4.1: 83 percent / MeONa / methanol
5.1: 95 percent / imidazole / CH2Cl2
6.1: 96 percent / DIBAL-H / toluene
7.1: 98 percent / PCC / CH2Cl2
8.1: 70 percent / BuLi / tetrahydrofuran
9.1: Pd(PPh3)2(OAc)2*CuI; Et2NH / dimethylformamide
9.2: 85 percent / TBAF / tetrahydrofuran
With
pyridine; 1H-imidazole; copper(l) iodide; n-butyllithium; bis(triphenylphosphine) palladium (Il) acetate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; sodium methylate; diisobutylaluminium hydride; diethylamine; triphenylphosphine; pyridinium chlorochromate; trichlorophosphate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
1.1: Dehydration / 2.1: Hydrolysis / 3.1: Acylation / 4.1: deprotection / 5.1: Etherification / 6.1: Reduction / 7.1: Oxidation / 8.1: Condensation / 9.1: Condensation / 9.2: deprotection;
DOI:10.1016/S0040-4039(99)02152-8