(R)-4-{(S)-1-[Hydroxy-(4-methoxy-benzyl)-amino]-but-3-enyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(R)-4-{(S)-1-[Hydroxy-(4-methoxy-benzyl)-amino]-but-3-enyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:745794-10-9
Molecular Formula:C₂₂H₃₄N₂O₅
Molecular Weight:406.522
Hs Code.:

Synonyms:(R)-4-{(S)-1-[Hydroxy-(4-methoxy-benzyl)-amino]-but-3-enyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of (R)-4-{(S)-1-[Hydroxy-(4-methoxy-benzyl)-amino]-but-3-enyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (R)-4-{(S)-1-[Hydroxy-(4-methoxy-benzyl)-amino]-but-3-enyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 2 articles about (R)-4-{(S)-1-[Hydroxy-(4-methoxy-benzyl)-amino]-but-3-enyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl 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:

: 102308-32-7
(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 745794-10-9
(R)-4-{(S)-1-[Hydroxy-(4-methoxy-benzyl)-amino]-but-3-enyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 8.1 g / MgSO₄ / CH₂Cl₂ / 20 °C

2: 87 percent / ZnBr₂ / tetrahydrofuran; diethyl ether / 4 h / -70 °C

With magnesium sulfate; zinc dibromide; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo0496547

Reference yield:

: 108149-63-9
4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 745794-10-9
(R)-4-{(S)-1-[Hydroxy-(4-methoxy-benzyl)-amino]-but-3-enyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 8.1 g / MgSO₄ / CH₂Cl₂ / 20 °C

3: 87 percent / ZnBr₂ / tetrahydrofuran; diethyl ether / 4 h / -70 °C

With oxalyl dichloride; magnesium sulfate; dimethyl sulfoxide; triethylamine; zinc dibromide; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Swern oxidation;
DOI:10.1021/jo0496547

Reference yield:

: 745794-10-9
(R)-4-{(S)-1-[Hydroxy-(4-methoxy-benzyl)-amino]-but-3-enyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: (1R,5S)-{5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]-2,3-dihydroxycyclopentyl}carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: Zn; Cu(OAc)2; AcOH / H₂O / 2 h / 70 °C

2: NaHCO₃ / H₂O; ethyl acetate / 20 °C

3: 8.64 g / p-TsOH*H₂O / methanol / 1 h / Heating

4: (COCl)2; DMSO; Et₃N / CH₂Cl₂

5: 93 percent / tetrahydrofuran / 20 °C

6: [Ru(PCy₃)2(=CHPh)Cl₂] / CH₂Cl₂ / 24 h / 35 °C

7: 78 percent / NaHCO₃; 3-chloroperbenzoic acid / CH₂Cl₂ / 24 h / 15 °C

8: H₂SO₄ / H₂O; dioxane / 10 °C

With copper diacetate; oxalyl dichloride; sulfuric acid; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; Grubbs catalyst first generation; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; 4: Swern oxidation / 6: ring-closing metathesis;
DOI:10.1021/jo0496547