(3R,3aS,7aR)-1-Benzyl-6-(toluene-4-sulfonyl)-3-((E)-4-trimethylsilanyl-but-2-enyl)-octahydro-pyrrolo[2,3-c]pyridin-7-ol

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Chemical Name:(3R,3aS,7aR)-1-Benzyl-6-(toluene-4-sulfonyl)-3-((E)-4-trimethylsilanyl-but-2-enyl)-octahydro-pyrrolo[2,3-c]pyridin-7-ol
CAS No.:133627-55-1
Molecular Formula:C₂₈H₄₀N₂O₃SSi
Molecular Weight:512.789
Hs Code.:

Synonyms:(3R,3aS,7aR)-1-Benzyl-6-(toluene-4-sulfonyl)-3-((E)-4-trimethylsilanyl-but-2-enyl)-octahydro-pyrrolo[2,3-c]pyridin-7-ol

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Chemical Property of (3R,3aS,7aR)-1-Benzyl-6-(toluene-4-sulfonyl)-3-((E)-4-trimethylsilanyl-but-2-enyl)-octahydro-pyrrolo[2,3-c]pyridin-7-ol

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Technology Process of (3R,3aS,7aR)-1-Benzyl-6-(toluene-4-sulfonyl)-3-((E)-4-trimethylsilanyl-but-2-enyl)-octahydro-pyrrolo[2,3-c]pyridin-7-ol

There total 17 articles about (3R,3aS,7aR)-1-Benzyl-6-(toluene-4-sulfonyl)-3-((E)-4-trimethylsilanyl-but-2-enyl)-octahydro-pyrrolo[2,3-c]pyridin-7-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: 93.0%

: 133627-54-0,133696-78-3
(3R,3aS,7aR)-1-Benzyl-6-(toluene-4-sulfonyl)-3-((E)-4-trimethylsilanyl-but-2-enyl)-octahydro-pyrrolo[2,3-c]pyridin-7-one

: 133627-55-1
(3R,3aS,7aR)-1-Benzyl-6-(toluene-4-sulfonyl)-3-((E)-4-trimethylsilanyl-but-2-enyl)-octahydro-pyrrolo[2,3-c]pyridin-7-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; -78 deg C to rt;
DOI:10.1021/jo00010a006

Reference yield:

: 21384-53-2,31907-91-2,196965-62-5
methyl 1-benzylaziridine-2-carboxylate

: 133627-55-1
(3R,3aS,7aR)-1-Benzyl-6-(toluene-4-sulfonyl)-3-((E)-4-trimethylsilanyl-but-2-enyl)-octahydro-pyrrolo[2,3-c]pyridin-7-ol

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) potassium trimethylsilanolate / 1.) THF, room temp., 2 h, 2.) CH₂Cl₂, 0 deg C

2: DMAP / CH₂Cl₂ / 2 h

3: 1,2-dichloro-benzene / 1.5 h / 320 °C

4: TsOH / methanol / 3 h / Ambient temperature

5: 1.) oxalyl chloride, DMSO, 2.) Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) -78 deg C to room temp., 30 min

6: tetrahydrofuran / 1 h / Ambient temperature

7: Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

9: 95 percent / Na, NH₃ / tetrahydrofuran; 2-methyl-propan-2-ol / 0.02 h

10: 71 percent / 1.) lithium bis(trimethylsilyl)amide, 2.) DMAP / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) 0 deg C to room temp., 1 h

11: 93 percent / DIBALH / CH₂Cl₂; hexane / 3 h / -78 deg C to room temp.

With dmap; oxalyl dichloride; potassium trimethylsilonate; ammonia; sodium; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; 1,2-dichloro-benzene; tert-butyl alcohol;
DOI:10.1021/jo00070a035

Reference yield:

: 133627-51-7
((3R,3aS,7aR)-1,6-Dibenzyl-7-oxo-octahydro-pyrrolo[2,3-c]pyridin-3-yl)-acetaldehyde

: 133627-55-1
(3R,3aS,7aR)-1-Benzyl-6-(toluene-4-sulfonyl)-3-((E)-4-trimethylsilanyl-but-2-enyl)-octahydro-pyrrolo[2,3-c]pyridin-7-ol

Guidance literature:: Multi-step reaction with 6 steps

1: tetrahydrofuran / 1 h / Ambient temperature

2: Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

4: 95 percent / Na, NH₃ / tetrahydrofuran; 2-methyl-propan-2-ol / 0.02 h

5: 71 percent / 1.) lithium bis(trimethylsilyl)amide, 2.) DMAP / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) 0 deg C to room temp., 1 h

6: 93 percent / DIBALH / CH₂Cl₂; hexane / 3 h / -78 deg C to room temp.

With dmap; ammonia; sodium; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; tert-butyl alcohol;
DOI:10.1021/jo00070a035