(4S,5S)-4-Benzyl-5-(2-ethoxycarbonyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(4S,5S)-4-Benzyl-5-(2-ethoxycarbonyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:742109-02-0
Molecular Formula:C₂₂H₃₃NO₅
Molecular Weight:391.508
Hs Code.:

Synonyms:(4S,5S)-4-Benzyl-5-(2-ethoxycarbonyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of (4S,5S)-4-Benzyl-5-(2-ethoxycarbonyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of (4S,5S)-4-Benzyl-5-(2-ethoxycarbonyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 8 articles about (4S,5S)-4-Benzyl-5-(2-ethoxycarbonyl-ethyl)-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: 90.0%

: (4S,5S)-4-Benzyl-5-((E)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 742109-02-0
(4S,5S)-4-Benzyl-5-(2-ethoxycarbonyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate;
DOI:10.1016/j.tetlet.2004.05.057

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 742109-02-0
(4S,5S)-4-Benzyl-5-(2-ethoxycarbonyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 0 - 20 °C

2: 89 percent / p-toluenesulfonic acid / CH₂Cl₂ / 20 °C

3: 76 percent / DIBAL-H / CH₂Cl₂ / -78 - 20 °C

4: 60 percent / tetrahydrofuran / 0 - 20 °C

5: 90 percent / H₂ / Pd/C / ethyl acetate; methanol

With hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 4: Wittig reaction;
DOI:10.1016/j.tetlet.2004.05.057

Reference yield:

: 54966-42-6,1466-22-4
ethyl 3-benzylacrylate

: 742109-02-0
(4S,5S)-4-Benzyl-5-(2-ethoxycarbonyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: (DHQ)2PHAL; K₂[OsO₂(OH)2]; LiOH / 2-methyl-propan-2-ol; H₂O / 0 - 20 °C

2: 87 percent / HCl / methanol / Heating

3: Et₃N / CH₂Cl₂ / 0 - 20 °C

4: 89 percent / p-toluenesulfonic acid / CH₂Cl₂ / 20 °C

5: 76 percent / DIBAL-H / CH₂Cl₂ / -78 - 20 °C

6: 60 percent / tetrahydrofuran / 0 - 20 °C

7: 90 percent / H₂ / Pd/C / ethyl acetate; methanol

With hydrogenchloride; lithium hydroxide; Hydroquinone 1,4-phthalazinediyl diether; K₂[OsO₂(OH)2]; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol; 6: Wittig reaction;
DOI:10.1016/j.tetlet.2004.05.057