tert-butyldimethylsilyl (7E,9Z,11Z,13E)-7,11-dideutero-12-(phenylsulfinyl)retinyl ether

Base Information

Chemical Name:tert-butyldimethylsilyl (7E,9Z,11Z,13E)-7,11-dideutero-12-(phenylsulfinyl)retinyl ether
CAS No.:269057-70-7
Molecular Formula:C₃₂H₄₈O₂SSi
Molecular Weight:526.868
Hs Code.:

Synonyms:tert-butyldimethylsilyl (7E,9Z,11Z,13E)-7,11-dideutero-12-(phenylsulfinyl)retinyl ether

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of tert-butyldimethylsilyl (7E,9Z,11Z,13E)-7,11-dideutero-12-(phenylsulfinyl)retinyl ether

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Technology Process of tert-butyldimethylsilyl (7E,9Z,11Z,13E)-7,11-dideutero-12-(phenylsulfinyl)retinyl ether

There total 6 articles about tert-butyldimethylsilyl (7E,9Z,11Z,13E)-7,11-dideutero-12-(phenylsulfinyl)retinyl ether 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: 77.0%

: 931-59-9
benzenesulfenyl chloride

: 269057-71-8
(2E,7E)-9-[(tert-butyldimethylsilyl)oxy]-1,1-dideutero-3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,7-dien-5-yn-4-ol

: 269057-70-7
tert-butyldimethylsilyl (7E,9Z,11Z,13E)-7,11-dideutero-12-(phenylsulfinyl)retinyl ether

Guidance literature:: With triethylamine; In tetrahydrofuran; at -78 - 25 ℃;
DOI:10.1021/jo991757f

Reference yield:

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 269057-70-7
tert-butyldimethylsilyl (7E,9Z,11Z,13E)-7,11-dideutero-12-(phenylsulfinyl)retinyl ether

Guidance literature:: Multi-step reaction with 6 steps

1: 99.9 percent / D₂O; NaH / pyridine / 4 h / 25 °C

2: 0.41 g / n-BuLi / tetrahydrofuran; hexane / -78 - 25 °C

3: 99.9 percent / DIBAL-H / tetrahydrofuran; toluene / 3 h / 0 °C

4: 89 percent / MnO₂ / CH₂Cl₂ / 3 h / 25 °C

5: 75 percent / n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

6: 77 percent / Et₃N / tetrahydrofuran / -78 - 25 °C

With manganese(IV) oxide; n-butyllithium; water-d2; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; pyridine; hexane; dichloromethane; toluene; 1: deuteration / 2: Condensation / 3: Reduction / 4: Oxidation / 5: Addition / 6: Addition;
DOI:10.1021/jo991757f

Reference yield:

: 269057-55-8
2,2-dideutero-2-(2,6,6-trimethylcyclohex-1-en-1-yl)ethanal

: 269057-70-7
tert-butyldimethylsilyl (7E,9Z,11Z,13E)-7,11-dideutero-12-(phenylsulfinyl)retinyl ether

Guidance literature:: Multi-step reaction with 5 steps

1: 0.41 g / n-BuLi / tetrahydrofuran; hexane / -78 - 25 °C

2: 99.9 percent / DIBAL-H / tetrahydrofuran; toluene / 3 h / 0 °C

3: 89 percent / MnO₂ / CH₂Cl₂ / 3 h / 25 °C

4: 75 percent / n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

5: 77 percent / Et₃N / tetrahydrofuran / -78 - 25 °C

With manganese(IV) oxide; n-butyllithium; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; 1: Condensation / 2: Reduction / 3: Oxidation / 4: Addition / 5: Addition;
DOI:10.1021/jo991757f