Technology Process of 5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbonyl)-4-hydroxy-1H-pyridin-2-one
There total 16 articles about 5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbonyl)-4-hydroxy-1H-pyridin-2-one which
guide to synthetic route it.
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synthetic route:
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882175-69-1
5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbonyl)-4-hydroxy-1-(4-methoxy-benzyloxy)-1H-pyridin-2-one
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882175-70-4
5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbonyl)-4-hydroxy-1H-pyridin-2-one
- Guidance literature:
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With
copper bis(oxazoline); tert-butylperoxy-4-nitrobenzoate;
In
acetone;
at 22 ℃;
DOI:10.3987/com-05-s(t)70
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882175-70-4
5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbonyl)-4-hydroxy-1H-pyridin-2-one
- Guidance literature:
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Multi-step reaction with 12 steps
1.1: 84 percent / imidazole / CH2Cl2
2.1: m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 / 0 °C
3.1: [C(CH3)2(CH2)3C(CH3)2]NLi / hexane; benzene / 0 - 20 °C
4.1: 87 percent / tri-n-butylphosphine / CH2Cl2 / 0.08 h / 22 °C
5.1: 86 percent / DIBAL / toluene
6.1: 97 percent / imidazole / CH2Cl2
7.1: toluene / 180 °C
8.1: PPTs; 4 Angstroem molecular sieves / CH2Cl2 / 20 °C
8.2: NaCNBH3 / acetic acid / 10 °C
9.1: 56 percent / benzotriazol-1-yloxytris(Me2N)phosphonium hexaFphosphate
10.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2
10.2: NaClO2; NaH2PO4 / acetonitrile; H2O; 2-methyl-propan-2-ol / 0 °C
10.3: 58 percent / 1,1'carbonyldiimidazole; NaH / dimethylformamide / 20 °C
11.1: 76 percent / BrCCl3; (Me2N)2C=NH / CH2Cl2 / 22 °C
12.1: 44 percent / tert-butylperoxy-4-nitrobenzoate; copper bis(oxazoline) complex / acetone / 22 °C
With
1H-imidazole; Bromotrichloromethane; tributylphosphine; 4 A molecular sieve; copper bis(oxazoline); tert-butylperoxy-4-nitrobenzoate; 2,2,6,6-tetramethylpiperidinyl-lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; N,N,N',N'-tetramethylguanidine;
In
hexane; dichloromethane; acetone; toluene; benzene;
12.1: Karash oxidation;
DOI:10.3987/com-05-s(t)70
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872472-36-1
3-((1S,2S,4aR,6S,8aS)-2,6-Dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-3-oxo-propionic acid
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882175-70-4
5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbonyl)-4-hydroxy-1H-pyridin-2-one
- Guidance literature:
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Multi-step reaction with 4 steps
1.1: 56 percent / benzotriazol-1-yloxytris(Me2N)phosphonium hexaFphosphate
2.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2
2.2: NaClO2; NaH2PO4 / acetonitrile; H2O; 2-methyl-propan-2-ol / 0 °C
2.3: 58 percent / 1,1'carbonyldiimidazole; NaH / dimethylformamide / 20 °C
3.1: 76 percent / BrCCl3; (Me2N)2C=NH / CH2Cl2 / 22 °C
4.1: 44 percent / tert-butylperoxy-4-nitrobenzoate; copper bis(oxazoline) complex / acetone / 22 °C
With
Bromotrichloromethane; copper bis(oxazoline); tert-butylperoxy-4-nitrobenzoate; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; N,N,N',N'-tetramethylguanidine;
In
dichloromethane; acetone;
4.1: Karash oxidation;
DOI:10.3987/com-05-s(t)70