(2S,3S,4S)-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-(iodomethyl)-4-(prop-1-en-2-yl)pyrrolidine

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Chemical Name:(2S,3S,4S)-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-(iodomethyl)-4-(prop-1-en-2-yl)pyrrolidine
CAS No.:952041-48-4
Molecular Formula:C₂₂H₃₆INOSi
Molecular Weight:485.524
Hs Code.:

Synonyms:(2S,3S,4S)-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-(iodomethyl)-4-(prop-1-en-2-yl)pyrrolidine

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Chemical Property of (2S,3S,4S)-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-(iodomethyl)-4-(prop-1-en-2-yl)pyrrolidine

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Technology Process of (2S,3S,4S)-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-(iodomethyl)-4-(prop-1-en-2-yl)pyrrolidine

There total 11 articles about (2S,3S,4S)-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-(iodomethyl)-4-(prop-1-en-2-yl)pyrrolidine 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: 90.0%

: 1332503-90-8
(S,E)-4-[benzyl(1-tert-butyldimethylsilyloxybut-3-en-2-yl)-amino]-2-methylbut-2-enyl acetate

: 952041-48-4
(2S,3S,4S)-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-(iodomethyl)-4-(prop-1-en-2-yl)pyrrolidine

Guidance literature:: (S,E)-4-[benzyl(1-tert-butyldimethylsilyloxybut-3-en-2-yl)-amino]-2-methylbut-2-enyl acetate; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro-trimethyl-silane; diethylzinc; In diethyl ether; hexane; at 20 ℃; for 6h; Inert atmosphere;

With iodine; In tetrahydrofuran; diethyl ether; hexane; for 0.5h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/jo201341q

Reference yield:

: 1303536-70-0
(S)-N-[1-hydroxy-4-(methylthio)butan-2-yl]benzamide

: 952041-48-4
(2S,3S,4S)-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-(iodomethyl)-4-(prop-1-en-2-yl)pyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1H-imidazole / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: sodium periodate / methanol; water; ethyl acetate / 3.5 h / 20 °C / Inert atmosphere

3.1: calcium carbonate / 1,2-dichloro-benzene / 5 h / Reflux; Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere; Reflux

4.2: 2 h / Inert atmosphere

5.1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro-trimethyl-silane; diethylzinc / diethyl ether; hexane / 6 h / 20 °C / Inert atmosphere

6.2: 0.5 h / Inert atmosphere

With 1H-imidazole; sodium periodate; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro-trimethyl-silane; diethylzinc; potassium carbonate; calcium carbonate; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 1,2-dichloro-benzene;
DOI:10.1021/jo201341q

Reference yield:

: 1332503-91-9
(S)-N-[1-(tert-butyldimethylsilyloxy)-4-(methylthio)butan-2-yl]benzamide

: 952041-48-4
(2S,3S,4S)-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-(iodomethyl)-4-(prop-1-en-2-yl)pyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium periodate / methanol; water; ethyl acetate / 3.5 h / 20 °C / Inert atmosphere

2.1: calcium carbonate / 1,2-dichloro-benzene / 5 h / Reflux; Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere; Reflux

3.2: 2 h / Inert atmosphere

4.1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro-trimethyl-silane; diethylzinc / diethyl ether; hexane / 6 h / 20 °C / Inert atmosphere

5.2: 0.5 h / Inert atmosphere

With sodium periodate; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro-trimethyl-silane; diethylzinc; potassium carbonate; calcium carbonate; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; hexane; water; ethyl acetate; N,N-dimethyl-formamide; 1,2-dichloro-benzene;
DOI:10.1021/jo201341q