7-(tert-butyl-dimethyl-silanyloxy)-3a-(hydroxy-phenyl-methyl)-2,2-dimethyl-7,7a-dihydro-3aH-benzo[1,3]dioxol-4-one

Base Information

Chemical Name:7-(tert-butyl-dimethyl-silanyloxy)-3a-(hydroxy-phenyl-methyl)-2,2-dimethyl-7,7a-dihydro-3aH-benzo[1,3]dioxol-4-one
CAS No.:313548-10-6
Molecular Formula:C₂₂H₃₂O₅Si
Molecular Weight:404.579
Hs Code.:

7-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3a-(hydroxy-phenyl-methyl)-2,2-dimethyl-7,7a-dihydro-3a<i>H</i>-benzo[1,3]dioxol-4-one

Synonyms:7-(tert-butyl-dimethyl-silanyloxy)-3a-(hydroxy-phenyl-methyl)-2,2-dimethyl-7,7a-dihydro-3aH-benzo[1,3]dioxol-4-one

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Chemical Property of 7-(tert-butyl-dimethyl-silanyloxy)-3a-(hydroxy-phenyl-methyl)-2,2-dimethyl-7,7a-dihydro-3aH-benzo[1,3]dioxol-4-one

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Technology Process of 7-(tert-butyl-dimethyl-silanyloxy)-3a-(hydroxy-phenyl-methyl)-2,2-dimethyl-7,7a-dihydro-3aH-benzo[1,3]dioxol-4-one

There total 12 articles about 7-(tert-butyl-dimethyl-silanyloxy)-3a-(hydroxy-phenyl-methyl)-2,2-dimethyl-7,7a-dihydro-3aH-benzo[1,3]dioxol-4-one 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: 46.0%

: 100-52-7
benzaldehyde

: 138913-29-8
(4R,5S,6R)-4-O-(tert-butyldimethylsilyl)-5,6-di-O-isopropylidenecyclohex-2-ene-1-one

: 313548-10-6
7-(tert-butyl-dimethyl-silanyloxy)-3a-(hydroxy-phenyl-methyl)-2,2-dimethyl-7,7a-dihydro-3aH-benzo[1,3]dioxol-4-one

: (1S,5R,6S,1'R,2'R,3'R,4'S)-5,2'-bis(tert-butyldimethylsiloxy)-1,6:3',4'-bis(O-isopropylidenedioxy)bicyclohexyl-3-ene-2,5'-dione

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(00)01312-5

Reference yield:

: 74293-60-0
(3aR,7R,7aS)-7-hydroxy-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one

: 313548-10-6
7-(tert-butyl-dimethyl-silanyloxy)-3a-(hydroxy-phenyl-methyl)-2,2-dimethyl-7,7a-dihydro-3aH-benzo[1,3]dioxol-4-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 98 percent / imidazole / dimethylformamide / 15 h / 20 °C

2.1: 53 percent / sodium borohydride / H₂O; tetrahydrofuran / 1 h / 20 °C

3.1: 98 percent / diethyl azodicarboxylate; triphenylphosphine / toluene; tetrahydrofuran / 3 h / 20 °C

4.1: 100 percent / potassium hydroxide / methanol / 3 h / 20 °C

5.1: 67 percent / diethyl azodicarboxylate; triphenylphosphine / toluene; tetrahydrofuran / 3 h / 20 °C

6.1: 92 percent / 3-chloroperoxybenzoic acid; sodium hydrogen carbonate / CH₂Cl₂ / 24 h / 20 °C

7.1: soduim borohydride; diphenyl diselenide / ethanol / 1 h / Heating

7.2: 78 percent / hydrogen peroxide / H₂O; ethanol / 1 h / Heating

8.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

9.1: 12 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

With 1H-imidazole; potassium hydroxide; sodium tetrahydroborate; diphenyl diselenide; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 3.1: Mitsunobu reaction / 8.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2005.10.082

Reference yield:

: 313547-95-4
(3R,4R,5R)-3-[(tert-butyl-dimethylsilyl)oxy]-4,5-(isopropylidenedioxy)-1-cyclohexanone

: 313548-10-6
7-(tert-butyl-dimethyl-silanyloxy)-3a-(hydroxy-phenyl-methyl)-2,2-dimethyl-7,7a-dihydro-3aH-benzo[1,3]dioxol-4-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 53 percent / sodium borohydride / H₂O; tetrahydrofuran / 1 h / 20 °C

2.1: 98 percent / diethyl azodicarboxylate; triphenylphosphine / toluene; tetrahydrofuran / 3 h / 20 °C

3.1: 100 percent / potassium hydroxide / methanol / 3 h / 20 °C

4.1: 67 percent / diethyl azodicarboxylate; triphenylphosphine / toluene; tetrahydrofuran / 3 h / 20 °C

5.1: 92 percent / 3-chloroperoxybenzoic acid; sodium hydrogen carbonate / CH₂Cl₂ / 24 h / 20 °C

6.1: soduim borohydride; diphenyl diselenide / ethanol / 1 h / Heating

6.2: 78 percent / hydrogen peroxide / H₂O; ethanol / 1 h / Heating

7.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

8.1: 12 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

With potassium hydroxide; sodium tetrahydroborate; diphenyl diselenide; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; 2.1: Mitsunobu reaction / 7.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2005.10.082