(3'S)-1-[3'-(4-methoxybenzyloxy)-2'-methylenebutyl]-4-acetoxyazetidin-2-one

Base Information

Chemical Name:(3'S)-1-[3'-(4-methoxybenzyloxy)-2'-methylenebutyl]-4-acetoxyazetidin-2-one
CAS No.:606972-11-6
Molecular Formula:C₁₈H₂₃NO₅
Molecular Weight:333.384
Hs Code.:

Synonyms:(3'S)-1-[3'-(4-methoxybenzyloxy)-2'-methylenebutyl]-4-acetoxyazetidin-2-one

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Chemical Property of (3'S)-1-[3'-(4-methoxybenzyloxy)-2'-methylenebutyl]-4-acetoxyazetidin-2-one

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Technology Process of (3'S)-1-[3'-(4-methoxybenzyloxy)-2'-methylenebutyl]-4-acetoxyazetidin-2-one

There total 8 articles about (3'S)-1-[3'-(4-methoxybenzyloxy)-2'-methylenebutyl]-4-acetoxyazetidin-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: 72.0%

: 606972-07-0
(3'S)-1-[3'-(4-methoxybenzyloxy)-2'-methylenebutyl]-4-vinyloxyazetidin-2-one

: 1-[2'-methylenebut-3'-one-1'-yl]-4-acetoxyazetidin-2-one

: 606972-11-6
(3'S)-1-[3'-(4-methoxybenzyloxy)-2'-methylenebutyl]-4-acetoxyazetidin-2-one

Guidance literature:: With silica gel; pyridinium chlorochromate; In dichloromethane; for 6h; Heating;
DOI:10.1016/S0040-4020(03)00939-6

Reference yield:

: 144401-98-9
(S)-2-(4-methoxybenzyloxy)propionic acid ethyl ester

: 606972-11-6
(3'S)-1-[3'-(4-methoxybenzyloxy)-2'-methylenebutyl]-4-acetoxyazetidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 88 percent / MeLi / tetrahydrofuran; various solvent(s) / 0.5 h / -78 °C

2.1: 82 percent / dimethylformamide / 2 h / 20 °C

3.1: BuLi / tetrahydrofuran; cyclohexane / -78 - 0 °C

3.2: tetrahydrofuran; cyclohexane / -78 - 20 °C

4.1: 4.3 g / K₂CO₃ / methanol / 3 h / 20 °C

5.1: 83 percent / Ph₃P; Br₂; imidazole / CH₂Cl₂ / 0.17 h / 0 °C

6.1: tetrabutylammonium hydrogen sulfate; BuLi / tetrahydrofuran; cyclohexane / -78 - -30 °C

6.2: 79 percent / tetrahydrofuran; cyclohexane / -78 - 0 °C

7.1: 72 percent / PCC; silica gel / CH₂Cl₂ / 6 h / Heating

With 1H-imidazole; n-butyllithium; methyllithium; bromine; tetra(n-butyl)ammonium hydrogensulfate; silica gel; potassium carbonate; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; 3.2: Wittig olefination reaction;
DOI:10.1016/S0040-4020(03)00939-6

Reference yield:

: 4-vinyloxyazetidin-2-one

: 606972-11-6
(3'S)-1-[3'-(4-methoxybenzyloxy)-2'-methylenebutyl]-4-acetoxyazetidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: tetrabutylammonium hydrogen sulfate; BuLi / tetrahydrofuran; cyclohexane / -78 - -30 °C

1.2: 79 percent / tetrahydrofuran; cyclohexane / -78 - 0 °C

2.1: 72 percent / PCC; silica gel / CH₂Cl₂ / 6 h / Heating

With n-butyllithium; tetra(n-butyl)ammonium hydrogensulfate; silica gel; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; cyclohexane;
DOI:10.1016/S0040-4020(03)00939-6