(SS)-2-(phenylsulfinyl)-3-(4-(triisopropylsilyloxy)pent-4-enyl)-1H-indole

Base Information

Chemical Name:(SS)-2-(phenylsulfinyl)-3-(4-(triisopropylsilyloxy)pent-4-enyl)-1H-indole
CAS No.:911136-28-2
Molecular Formula:C₂₈H₃₉NO₂SSi
Molecular Weight:481.775
Hs Code.:

Synonyms:(SS)-2-(phenylsulfinyl)-3-(4-(triisopropylsilyloxy)pent-4-enyl)-1H-indole

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Chemical Property of (SS)-2-(phenylsulfinyl)-3-(4-(triisopropylsilyloxy)pent-4-enyl)-1H-indole

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Technology Process of (SS)-2-(phenylsulfinyl)-3-(4-(triisopropylsilyloxy)pent-4-enyl)-1H-indole

There total 10 articles about (SS)-2-(phenylsulfinyl)-3-(4-(triisopropylsilyloxy)pent-4-enyl)-1H-indole 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: 70.0%

: 911136-48-6
(SS)-5-(2-(phenylsulfinyl)-1H-indol-3-yl)pentan-2-one

: 13154-24-0
triisopropylsilyl chloride

: 911136-28-2
(SS)-2-(phenylsulfinyl)-3-(4-(triisopropylsilyloxy)pent-4-enyl)-1H-indole

Guidance literature:: (SS)-5-(2-(phenylsulfinyl)-1H-indol-3-yl)pentan-2-one; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

triisopropylsilyl chloride; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2.5h;
DOI:10.1021/ol0617244

Reference yield:

: 4-(2-bromo-1H-indol-3-yl)-butyric acid methyl ester

: 911136-28-2
(SS)-2-(phenylsulfinyl)-3-(4-(triisopropylsilyloxy)pent-4-enyl)-1H-indole

Guidance literature:: Multi-step reaction with 9 steps

1.1: DMAP / CH₂Cl₂ / 1.17 h / 20 °C

2.1: DIBAL / hexane; CH₂Cl₂; tetrahydrofuran / -78 - 20 °C

3.1: 23.08 g / imidazole / CH₂Cl₂ / 15 h / 20 °C

4.1: t-BuLi / tetrahydrofuran; pentane / 0.08 h / -78 °C

4.2: 60 percent / tetrahydrofuran; pentane / -78 - 20 °C

5.1: TBAF / tetrahydrofuran / 15 h / 20 °C

6.1: 590 mg / tetrapropylammonium perruthenate; N-methyl morpholine N-oxide / CH₂Cl₂ / 1 h

7.1: tetrahydrofuran / 1 h / 20 °C

8.1: 173 mg / tetrapropylammonium perruthenate; N-methyl morpholine N-oxide / CH₂Cl₂ / 1 h

9.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

9.2: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C

With 1H-imidazole; dmap; n-butyllithium; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; tert.-butyl lithium; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; pentane;
DOI:10.1021/ol0617244

Reference yield:

: 911136-47-5
4-(2-benzenesulfinyl-1H-indol-3-yl)-butyraldehyde

: 911136-28-2
(SS)-2-(phenylsulfinyl)-3-(4-(triisopropylsilyloxy)pent-4-enyl)-1H-indole

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 1 h / 20 °C

2.1: 173 mg / tetrapropylammonium perruthenate; N-methyl morpholine N-oxide / CH₂Cl₂ / 1 h

3.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C

With n-butyllithium; tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0617244