(3S,3aS,4R,5S,7aS)-3a-Benzo[1,3]dioxol-5-yl-1-methyl-5-phenylselanyl-3-trimethylsilanyloxy-octahydro-indol-4-ol

Base Information

Chemical Name:(3S,3aS,4R,5S,7aS)-3a-Benzo[1,3]dioxol-5-yl-1-methyl-5-phenylselanyl-3-trimethylsilanyloxy-octahydro-indol-4-ol
CAS No.:123190-83-0
Molecular Formula:C₂₅H₃₃NO₄SeSi
Molecular Weight:518.587
Hs Code.:

Synonyms:(3S,3aS,4R,5S,7aS)-3a-Benzo[1,3]dioxol-5-yl-1-methyl-5-phenylselanyl-3-trimethylsilanyloxy-octahydro-indol-4-ol

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Chemical Property of (3S,3aS,4R,5S,7aS)-3a-Benzo[1,3]dioxol-5-yl-1-methyl-5-phenylselanyl-3-trimethylsilanyloxy-octahydro-indol-4-ol

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Technology Process of (3S,3aS,4R,5S,7aS)-3a-Benzo[1,3]dioxol-5-yl-1-methyl-5-phenylselanyl-3-trimethylsilanyloxy-octahydro-indol-4-ol

There total 8 articles about (3S,3aS,4R,5S,7aS)-3a-Benzo[1,3]dioxol-5-yl-1-methyl-5-phenylselanyl-3-trimethylsilanyloxy-octahydro-indol-4-ol 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: 81.0%

: 123190-82-9
(3S,3aR,5S,7aS)-3a-Benzo[1,3]dioxol-5-yl-1-methyl-5-phenylselanyl-3-trimethylsilanyloxy-octahydro-indol-4-one

: 123190-83-0
(3S,3aS,4R,5S,7aS)-3a-Benzo[1,3]dioxol-5-yl-1-methyl-5-phenylselanyl-3-trimethylsilanyloxy-octahydro-indol-4-ol

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.25h;
DOI:10.1016/S0040-4039(01)80272-0

Reference yield:

: 5707-04-0
Phenylselenyl chloride

: 123190-83-0
(3S,3aS,4R,5S,7aS)-3a-Benzo[1,3]dioxol-5-yl-1-methyl-5-phenylselanyl-3-trimethylsilanyloxy-octahydro-indol-4-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 78 percent / CH₂Cl₂ / 1 h / 0 °C

2: 81 percent / i-Bu₂AlH / toluene / 0.25 h / -78 °C

With diisobutylaluminium hydride; In dichloromethane; toluene;
DOI:10.1016/S0040-4039(01)80272-0

Reference yield:

: 57134-53-9
3,4-methylenedioxyphenylethyne

: 123190-83-0
(3S,3aS,4R,5S,7aS)-3a-Benzo[1,3]dioxol-5-yl-1-methyl-5-phenylselanyl-3-trimethylsilanyloxy-octahydro-indol-4-ol

Guidance literature:: Multi-step reaction with 6 steps

2: 94 percent / copper(II)triflate / tetrahydrofuran / 2 h / Heating

3: 1) HBF₃*Et₂O, 2) 30percent H₂O₂, KF / 1) CH₂Cl₂, room temp., 2 h, 2) DMF, 60 deg C, 7 h

4: 95 percent / NEt₃ / CH₂Cl₂ / 1 h / 0 °C

5: 78 percent / CH₂Cl₂ / 1 h / 0 °C

6: 81 percent / i-Bu₂AlH / toluene / 0.25 h / -78 °C

With tetrafluoroboric acid diethyl ether; potassium fluoride; dihydrogen peroxide; copper(II) bis(trifluoromethanesulfonate); diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/S0040-4039(01)80272-0