Technology Process of Phenyl-carbamic acid (2S,4aR,5S,8aR)-5-[(3E,7E)-4,8-dimethyl-10-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-deca-3,7-dienyl]-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl ester
There total 12 articles about Phenyl-carbamic acid (2S,4aR,5S,8aR)-5-[(3E,7E)-4,8-dimethyl-10-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-deca-3,7-dienyl]-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl ester which
guide to synthetic route it.
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synthetic route:
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373389-60-7
Phenyl-carbamic acid (2S,4aS,5R,8aR)-5-[(3E,7E)-4,8-dimethyl-10-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-deca-3,7-dienyl]-1,1,4a-trimethyl-6-oxo-decahydro-naphthalen-2-yl ester
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373389-65-2
Phenyl-carbamic acid (2S,4aR,5S,8aR)-5-[(3E,7E)-4,8-dimethyl-10-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-deca-3,7-dienyl]-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl ester
- Guidance literature:
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With
potassium tert-butylate;
In
tetrahydrofuran; benzene;
for 2h;
Heating;
DOI:10.1021/ol016543a
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373389-65-2
Phenyl-carbamic acid (2S,4aR,5S,8aR)-5-[(3E,7E)-4,8-dimethyl-10-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-deca-3,7-dienyl]-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl ester
- Guidance literature:
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Multi-step reaction with 12 steps
1.1: 72 percent / MeSO2NH2; K2OsO4*2H2O; K3Fe(CN)6 / chiral monocinchona derivative C70H63N5O3; K2CO3 / 2-methyl-propan-2-ol; H2O / 4 h / 0 °C
2.1: p-TsOH / 0.5 h / 23 °C
3.1: K2CO3 / methanol / 1 h / 23 °C
4.1: MeSO2Cl; Et3N / CH2Cl2 / 1.5 h / -42 - 0 °C
4.2: LiBr / tetrahydrofuran / 1 h / 0 °C
5.1: LDA; CuI / tetrahydrofuran / -110 - -30 °C
5.2: 92 percent / tetrahydrofuran / 1 h / -30 °C
6.1: LiAlH4 / diethyl ether / 0.5 h / Heating
7.1: Ph3P; imidazole; I2 / CH2Cl2 / 0.5 h / 23 °C
8.1: 1.10 g / dimethylformamide / 24 h / 23 °C
9.1: BuLi / tetrahydrofuran; diethyl ether; hexane / 0.17 h / -78 °C
9.2: 75 percent / tetrahydrofuran; diethyl ether; hexane / -78 - 0 °C
10.1: Me2AlCl2 / CH2Cl2 / 0.25 h / -94 °C
10.2: TBAF / tetrahydrofuran / 15 h / 50 °C
10.3: 75 percent / KOH / methanol / 3 h / Heating
11.1: 75 percent / pyridine / 12 h / 23 °C
12.1: 90 percent / KOtBu / benzene; tetrahydrofuran / 2 h / Heating
With
1H-imidazole; potassium osmate(VI); copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; methanesulfonamide; Me2AlCl2; potassium tert-butylate; iodine; potassium carbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); lithium diisopropyl amide;
chiral monocinchona derivative C70H63N5O3; potassium carbonate;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1021/ol016543a
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373389-65-2
Phenyl-carbamic acid (2S,4aR,5S,8aR)-5-[(3E,7E)-4,8-dimethyl-10-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-deca-3,7-dienyl]-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl ester
- Guidance literature:
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Multi-step reaction with 10 steps
1.1: K2CO3 / methanol / 1 h / 23 °C
2.1: MeSO2Cl; Et3N / CH2Cl2 / 1.5 h / -42 - 0 °C
2.2: LiBr / tetrahydrofuran / 1 h / 0 °C
3.1: LDA; CuI / tetrahydrofuran / -110 - -30 °C
3.2: 92 percent / tetrahydrofuran / 1 h / -30 °C
4.1: LiAlH4 / diethyl ether / 0.5 h / Heating
5.1: Ph3P; imidazole; I2 / CH2Cl2 / 0.5 h / 23 °C
6.1: 1.10 g / dimethylformamide / 24 h / 23 °C
7.1: BuLi / tetrahydrofuran; diethyl ether; hexane / 0.17 h / -78 °C
7.2: 75 percent / tetrahydrofuran; diethyl ether; hexane / -78 - 0 °C
8.1: Me2AlCl2 / CH2Cl2 / 0.25 h / -94 °C
8.2: TBAF / tetrahydrofuran / 15 h / 50 °C
8.3: 75 percent / KOH / methanol / 3 h / Heating
9.1: 75 percent / pyridine / 12 h / 23 °C
10.1: 90 percent / KOtBu / benzene; tetrahydrofuran / 2 h / Heating
With
1H-imidazole; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; Me2AlCl2; potassium tert-butylate; iodine; potassium carbonate; methanesulfonyl chloride; triethylamine; triphenylphosphine; lithium diisopropyl amide;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ol016543a