2-{(E)-4-[(1S,2S)-2-(4-Methoxy-benzyloxymethyl)-cyclopropyl]-but-3-en-1-ynyl}-oxazole-4-carboxylic acid ethyl ester

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Chemical Name:2-{(E)-4-[(1S,2S)-2-(4-Methoxy-benzyloxymethyl)-cyclopropyl]-but-3-en-1-ynyl}-oxazole-4-carboxylic acid ethyl ester
CAS No.:617705-31-4
Molecular Formula:C₂₂H₂₃NO₅
Molecular Weight:381.428
Hs Code.:

Synonyms:2-{(E)-4-[(1S,2S)-2-(4-Methoxy-benzyloxymethyl)-cyclopropyl]-but-3-en-1-ynyl}-oxazole-4-carboxylic acid ethyl ester

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Chemical Property of 2-{(E)-4-[(1S,2S)-2-(4-Methoxy-benzyloxymethyl)-cyclopropyl]-but-3-en-1-ynyl}-oxazole-4-carboxylic acid ethyl ester

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Technology Process of 2-{(E)-4-[(1S,2S)-2-(4-Methoxy-benzyloxymethyl)-cyclopropyl]-but-3-en-1-ynyl}-oxazole-4-carboxylic acid ethyl ester

There total 5 articles about 2-{(E)-4-[(1S,2S)-2-(4-Methoxy-benzyloxymethyl)-cyclopropyl]-but-3-en-1-ynyl}-oxazole-4-carboxylic acid ethyl ester 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: 49.0%

: 617705-26-7
2-ethynyloxazole-4-carboxylic acid ethyl ester

: 617705-30-3
1-[({(1S,2R)-2-[(E)-2-iodoethenyl]cyclopropyl}methoxy)methyl]-4-methoxybenzene

: 617705-31-4
2-{(E)-4-[(1S,2S)-2-(4-Methoxy-benzyloxymethyl)-cyclopropyl]-but-3-en-1-ynyl}-oxazole-4-carboxylic acid ethyl ester

Guidance literature:: 1-[({(1S,2R)-2-[(E)-2-iodoethenyl]cyclopropyl}methoxy)methyl]-4-methoxybenzene; With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide;

2-ethynyloxazole-4-carboxylic acid ethyl ester; at 20 ℃;
DOI:10.1016/S0040-4020(03)00916-5

Reference yield:

: 143833-81-2
(Z)-4-(4-methoxybenzyloxy)but-2-en-1-ol

: 617705-31-4
2-{(E)-4-[(1S,2S)-2-(4-Methoxy-benzyloxymethyl)-cyclopropyl]-but-3-en-1-ynyl}-oxazole-4-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 81 percent / Et₂Zn; chiral dioxaborolane complex / CH₂Cl₂; heptane / 4.5 h / 0 °C

2.1: 88 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h / 20 °C

3.1: 49 percent / CrCl₂ / tetrahydrofuran / 4 h / 0 °C

4.1: CuI; Et₃N / Pd(PPh₃)2Cl₂ / dimethylformamide

4.2: 49 percent / 20 °C

With chromium dichloride; copper(l) iodide; chiral dioxaborolane; diethylzinc; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; n-heptane; dichloromethane; N,N-dimethyl-formamide; 1.1: asymmetric Charette cyclopropanation / 3.1: Takai reaction / 4.2: Sonogashira cross-coupling;
DOI:10.1016/S0040-4020(03)00916-5

Reference yield:

: 181633-60-3
ethyl 2-formyl-1, 3-oxazole-4-carboxylate

: 617705-31-4
2-{(E)-4-[(1S,2S)-2-(4-Methoxy-benzyloxymethyl)-cyclopropyl]-but-3-en-1-ynyl}-oxazole-4-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 50 percent / K₂CO₃ / ethanol / 0 °C

2.1: CuI; Et₃N / Pd(PPh₃)2Cl₂ / dimethylformamide

2.2: 49 percent / 20 °C

With copper(l) iodide; potassium carbonate; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In ethanol; N,N-dimethyl-formamide; 2.2: Sonogashira cross-coupling;
DOI:10.1016/S0040-4020(03)00916-5