Technology Process of (4S,4aS,5S,6S,7R,8R,11S,12S,12aR)-6,12-Dibenzyloxy-11-(dicyclohexylmethylsiloxy)-4,5-(isopropylidenedioxy)-4a,8,13,13-tetramethyl-1-methylenetetradecahydro-7,11-methanobenzocyclodecene-7,8-diol
There total 17 articles about (4S,4aS,5S,6S,7R,8R,11S,12S,12aR)-6,12-Dibenzyloxy-11-(dicyclohexylmethylsiloxy)-4,5-(isopropylidenedioxy)-4a,8,13,13-tetramethyl-1-methylenetetradecahydro-7,11-methanobenzocyclodecene-7,8-diol 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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194420-23-0
(1S,2S,3S,6S,7S,8R,12S)-3,7-Dibenzyloxy-6-(dicyclohexylmethylsiloxy)-2,12-(isopropylidenedioxy)-1,5,5-trimethyl-9-methylene-6-(3-oxobutyl)bicyclo[6.4.0]dodecan-4-one
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194420-24-1
(4S,4aS,5S,6S,7R,8R,11S,12S,12aR)-6,12-Dibenzyloxy-11-(dicyclohexylmethylsiloxy)-4,5-(isopropylidenedioxy)-4a,8,13,13-tetramethyl-1-methylenetetradecahydro-7,11-methanobenzocyclodecene-7,8-diol
- Guidance literature:
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With
lithium aluminium tetrahydride; titanium tetrachloride;
In
tetrahydrofuran;
at 35 ℃;
DOI:10.1246/cl.1998.1
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202340-82-7
(1R,2S,3S,5R,6R,7S,8S,9S)-2,6-Dibenzyloxy-3-(3-butenyl)-7,9-(isopropylidenedioxy)-4,4,8-trimethyl-12-methylenebicyclo[6.4.0]dodecan-3,5-diol
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194420-24-1
(4S,4aS,5S,6S,7R,8R,11S,12S,12aR)-6,12-Dibenzyloxy-11-(dicyclohexylmethylsiloxy)-4,5-(isopropylidenedioxy)-4a,8,13,13-tetramethyl-1-methylenetetradecahydro-7,11-methanobenzocyclodecene-7,8-diol
- Guidance literature:
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Multi-step reaction with 5 steps
1: 100 percent / pyridine / toluene / 0.25 h / 0 °C
2: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 3 h / -45 °C
3: 91 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 1 h / 20 °C
4: 98 percent / PdCl2; H2O / dimethylformamide / 2.5 h / 20 °C
5: 63 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.08 h / 45 °C
With
pyridine; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; water; titanium chloride; palladium dichloride;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
1: Etherification / 2: Methylation / 3: Oxidation / 4: Oxidation / 5: Cyclization;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f
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222726-95-6
(1R,2S,3R,5R,6S,7S,8S,9S)-2,6-Dibenzyloxy-5-(tert-butyldimethylsiloxy)-7,9-(isopropylidenedioxy)-4,4,8-trimethyl-12-methylenebicyclo[6.4.0]dodecan-3-ol
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194420-24-1
(4S,4aS,5S,6S,7R,8R,11S,12S,12aR)-6,12-Dibenzyloxy-11-(dicyclohexylmethylsiloxy)-4,5-(isopropylidenedioxy)-4a,8,13,13-tetramethyl-1-methylenetetradecahydro-7,11-methanobenzocyclodecene-7,8-diol
- Guidance literature:
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Multi-step reaction with 8 steps
1.1: 90 percent / PDC / CH2Cl2 / 16 h / 20 °C
2.1: s-BuLi / cyclohexane / 0.42 h / -23 °C
2.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C
3.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C
4.1: 100 percent / pyridine / toluene / 0.25 h / 0 °C
5.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 3 h / -45 °C
6.1: 91 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 1 h / 20 °C
7.1: 98 percent / PdCl2; H2O / dimethylformamide / 2.5 h / 20 °C
8.1: 63 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.08 h / 45 °C
With
pyridine; lithium aluminium tetrahydride; dipyridinium dichromate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; sec.-butyllithium; titanium chloride; palladium dichloride;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; acetonitrile;
1.1: Oxidation / 2.1: Metallation / 2.2: Alkylation / 3.1: Substitution / 4.1: Etherification / 5.1: Methylation / 6.1: Oxidation / 7.1: Oxidation / 8.1: Cyclization;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f