(1R,3aR,4S,5R,7aS)-5-ethynyl-1-[(4-methoxybenzyl)oxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl][4-(trimethylsilyl)phenyl]methanone

Base Information

Chemical Name:(1R,3aR,4S,5R,7aS)-5-ethynyl-1-[(4-methoxybenzyl)oxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl][4-(trimethylsilyl)phenyl]methanone
CAS No.:1309113-39-0
Molecular Formula:C₃₃H₄₂O₃Si
Molecular Weight:514.78
Hs Code.:

(1R,3aR,4S,5R,7aS)-5-ethynyl-1-[(4-methoxybenzyl)oxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl][4-(trimethylsilyl)phenyl]methanone

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Chemical Property of (1R,3aR,4S,5R,7aS)-5-ethynyl-1-[(4-methoxybenzyl)oxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl][4-(trimethylsilyl)phenyl]methanone

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Technology Process of (1R,3aR,4S,5R,7aS)-5-ethynyl-1-[(4-methoxybenzyl)oxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl][4-(trimethylsilyl)phenyl]methanone

There total 18 articles about (1R,3aR,4S,5R,7aS)-5-ethynyl-1-[(4-methoxybenzyl)oxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl][4-(trimethylsilyl)phenyl]methanone 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:

Reference yield:

: 854490-31-6
(E)-diethyl (2-methyl-5-(trimethylsilyl)pent-2-en-4-yn-1-yl)phosphonate

: 1309113-38-9
(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][4-(trimethylsilyl)phenyl]methanone

: 1309113-39-0
(1R,3aR,4S,5R,7aS)-5-ethynyl-1-[(4-methoxybenzyl)oxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl][4-(trimethylsilyl)phenyl]methanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / -30 °C / Molecular sieve; Inert atmosphere

4.1: N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / -78 - -50 °C / Inert atmosphere

5.1: 4-methylmorpholine N-oxide / dichloromethane / 5 h / -40 °C / Molecular sieve

With tetrapropylammonium perruthennate; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; 1.1: Horner-Wadsworth-Emmons olefination / 1.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1002/anie.201006880

Reference yield:

: 1309113-16-3
(E)-7-[(tert-butyldimethylsilyl)oxy]-4,4-dimethyl-2-methylenehept-5-en-1-ol

: 1309113-38-9
(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][4-(trimethylsilyl)phenyl]methanone

: 1309113-39-0
(1R,3aR,4S,5R,7aS)-5-ethynyl-1-[(4-methoxybenzyl)oxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl][4-(trimethylsilyl)phenyl]methanone

Guidance literature:: Multi-step reaction with 10 steps

1.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / decane; dichloromethane / 20 h / -25 °C / Molecular sieve; Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 2 h / 20 °C

4.1: diisobutylaluminium hydride / toluene / -78 - 20 °C / Inert atmosphere

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3 h / 0 °C

6.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

6.2: -78 - 20 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

8.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / -30 °C / Molecular sieve; Inert atmosphere

9.1: N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / -78 - -50 °C / Inert atmosphere

10.1: 4-methylmorpholine N-oxide / dichloromethane / 5 h / -40 °C / Molecular sieve

With titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; diethyl (2S,3S)-tartrate; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; decane; dichloromethane; toluene; 6.1: Horner-Wadsworth-Emmons olefination / 6.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1002/anie.201006880

Reference yield:

: 4-{[(4-methoxybenzyl)oxy]methyl}-2,2-dimethylpent-4-enal

: 1309113-38-9
(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][4-(trimethylsilyl)phenyl]methanone

: 1309113-39-0
(1R,3aR,4S,5R,7aS)-5-ethynyl-1-[(4-methoxybenzyl)oxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl][4-(trimethylsilyl)phenyl]methanone

Guidance literature:: Multi-step reaction with 14 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 50 °C / Inert atmosphere

1.2: 2.5 h / 20 - 80 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / -78 - 20 °C / Inert atmosphere

3.1: dmap / dichloromethane / 20 °C / Inert atmosphere

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C / pH 7 / aq. phosphate buffer

5.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / decane; dichloromethane / 20 h / -25 °C / Molecular sieve; Inert atmosphere

6.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

7.1: triethylamine / dichloromethane / 2 h / 20 °C

8.1: diisobutylaluminium hydride / toluene / -78 - 20 °C / Inert atmosphere

9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3 h / 0 °C

10.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

10.2: -78 - 20 °C / Inert atmosphere

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

12.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / -30 °C / Molecular sieve; Inert atmosphere

13.1: N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / -78 - -50 °C / Inert atmosphere

14.1: 4-methylmorpholine N-oxide / dichloromethane / 5 h / -40 °C / Molecular sieve

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; diethyl (2S,3S)-tartrate; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; decane; dichloromethane; toluene; mineral oil; 1.1: Horner-Wadsworth-Emmons olefination / 1.2: Horner-Wadsworth-Emmons olefination / 10.1: Horner-Wadsworth-Emmons olefination / 10.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1002/anie.201006880