Technology Process of [4-(benzyldimethylsilyl)phenyl][(1R,3aS,4R,5S,7aR)-5-ethynyl-1-hydroxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl]methanone
There total 15 articles about [4-(benzyldimethylsilyl)phenyl][(1R,3aS,4R,5S,7aR)-5-ethynyl-1-hydroxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl]methanone which
guide to synthetic route it.
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synthetic route:
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1531626-55-7
[4-(benzyldimethylsilyl)phenyl]{(1R,3aS,4R,5S,7aR)-5-ethynyl-1-[(4-methoxybenzyl)oxy]-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl}methanone
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1531626-58-0
[4-(benzyldimethylsilyl)phenyl][(1R,3aS,4R,5S,7aR)-5-ethynyl-1-hydroxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl]methanone
- Guidance literature:
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With
2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
dichloromethane;
at 0 ℃;
for 0.833333h;
pH=7;
DOI:10.1021/ol403441c
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1531626-58-0
[4-(benzyldimethylsilyl)phenyl][(1R,3aS,4R,5S,7aR)-5-ethynyl-1-hydroxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl]methanone
- Guidance literature:
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Multi-step reaction with 10 steps
1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C
2.1: titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane / 20 h / -25 °C
2.2: Molecular sieve
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h
4.1: PPTA / dichloromethane / 2 h / 20 °C
4.2: -78 - 20 °C
5.1: dmap; sodium hydrogencarbonate / dichloromethane / 3 h / 0 °C
6.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C
6.2: -78 - 20 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
8.1: NMO; tetrapropylammonium perruthennate / dichloromethane / 3 h / -30 °C / Molecular sieve
8.2: 0.42 h / -90 - -70 °C
9.1: tetrapropylammonium perruthennate; magnesium bromide ethyl etherate / dichloromethane / 3 h / 0 °C
10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.83 h / 0 °C / pH 7
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; NMO; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydrogencarbonate; magnesium bromide ethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; dichloromethane;
DOI:10.1021/ol403441c
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1531626-58-0
[4-(benzyldimethylsilyl)phenyl][(1R,3aS,4R,5S,7aR)-5-ethynyl-1-hydroxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl]methanone
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane / 20 h / -25 °C
1.2: Molecular sieve
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h
3.1: PPTA / dichloromethane / 2 h / 20 °C
3.2: -78 - 20 °C
4.1: dmap; sodium hydrogencarbonate / dichloromethane / 3 h / 0 °C
5.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C
5.2: -78 - 20 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
7.1: NMO; tetrapropylammonium perruthennate / dichloromethane / 3 h / -30 °C / Molecular sieve
7.2: 0.42 h / -90 - -70 °C
8.1: tetrapropylammonium perruthennate; magnesium bromide ethyl etherate / dichloromethane / 3 h / 0 °C
9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.83 h / 0 °C / pH 7
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; NMO; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydrogencarbonate; magnesium bromide ethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; dichloromethane;
DOI:10.1021/ol403441c