(4R,6S,1'S)-6-<2-(1-Benzyl-1H-indol-3-yl)-1-iodoethyl>-4-<(tert-butyldimethylsilyl)oxy>tetrahydro-2H-pyran-2-one

Base Information

Chemical Name:(4R,6S,1'S)-6-<2-(1-Benzyl-1H-indol-3-yl)-1-iodoethyl>-4-<(tert-butyldimethylsilyl)oxy>tetrahydro-2H-pyran-2-one
CAS No.:171365-23-4
Molecular Formula:C₂₈H₃₆INO₃Si
Molecular Weight:589.589
Hs Code.:

Synonyms:(4R,6S,1'S)-6-<2-(1-Benzyl-1H-indol-3-yl)-1-iodoethyl>-4-<(tert-butyldimethylsilyl)oxy>tetrahydro-2H-pyran-2-one

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Chemical Property of (4R,6S,1'S)-6-<2-(1-Benzyl-1H-indol-3-yl)-1-iodoethyl>-4-<(tert-butyldimethylsilyl)oxy>tetrahydro-2H-pyran-2-one

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Technology Process of (4R,6S,1'S)-6-<2-(1-Benzyl-1H-indol-3-yl)-1-iodoethyl>-4-<(tert-butyldimethylsilyl)oxy>tetrahydro-2H-pyran-2-one

There total 7 articles about (4R,6S,1'S)-6-<2-(1-Benzyl-1H-indol-3-yl)-1-iodoethyl>-4-<(tert-butyldimethylsilyl)oxy>tetrahydro-2H-pyran-2-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: 31.0%

: 171365-22-3
(3R,Z)-7-(1-Benzyl-1H-indol-3-yl)-3-<(tert-butyldimethylsilyl)oxy>-5-heptenoic acid

: 171365-23-4
(4R,6S,1'S)-6-<2-(1-Benzyl-1H-indol-3-yl)-1-iodoethyl>-4-<(tert-butyldimethylsilyl)oxy>tetrahydro-2H-pyran-2-one

: 171484-69-8
(4R,6R,1'R)-6-<2-(1-Benzyl-1H-indol-3-yl)-1-iodoethyl>-4-<(tert-butyldimethylsilyl)oxy>tetrahydro-2H-pyran-2-one

Guidance literature:: With iodine; sodium hydrogencarbonate; potassium iodide; In tetrahydrofuran; for 3h; Ambient temperature;

Reference yield:

: 13137-14-9
acetic acid 2-(1H-indol-3-yl)ethyl ester

: 171365-23-4
(4R,6S,1'S)-6-<2-(1-Benzyl-1H-indol-3-yl)-1-iodoethyl>-4-<(tert-butyldimethylsilyl)oxy>tetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 50 percent / NaH / 1,2-dimethoxy-ethane / 1.) r.t., 30 min, 2.) 1 h

2: 96 percent / NaOMe / methanol / 0.17 h / Ambient temperature; i18

3: 82 percent / pyridine / 1.) 5 deg C, 1 h, 2.) r.t., 2 h

4: 68 percent / 10percent aq. HCl / CH₂Cl₂ / 0.25 h / Ambient temperature

5: 60 percent / acetonitrile / 65 h / Heating

6: 64 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -20 deg C, 1 h, 2.) -70 deg C, 30 min; -20 deg C, 2 h; r.t., 1 h

7: 97 percent / 2 M aq. NaOH / ethanol / 4 h / 70 °C

8: 33 percent / aq. KI, NaHCO₃, I₂ / tetrahydrofuran / 3 h / Ambient temperature

With pyridine; hydrogenchloride; sodium hydroxide; n-butyllithium; iodine; sodium methylate; sodium hydride; sodium hydrogencarbonate; potassium iodide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; acetonitrile;

Reference yield:

: 14503-49-2
2-(1-Benzyl-1H-indol-3-yl)ethanol tosylate

: 171365-23-4
(4R,6S,1'S)-6-<2-(1-Benzyl-1H-indol-3-yl)-1-iodoethyl>-4-<(tert-butyldimethylsilyl)oxy>tetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 68 percent / 10percent aq. HCl / CH₂Cl₂ / 0.25 h / Ambient temperature

2: 60 percent / acetonitrile / 65 h / Heating

3: 64 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -20 deg C, 1 h, 2.) -70 deg C, 30 min; -20 deg C, 2 h; r.t., 1 h

4: 97 percent / 2 M aq. NaOH / ethanol / 4 h / 70 °C

5: 33 percent / aq. KI, NaHCO₃, I₂ / tetrahydrofuran / 3 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; n-butyllithium; iodine; sodium hydrogencarbonate; potassium iodide; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetonitrile;