(S)-tert-butyl 4-(3-(benzyloxy)-4-formylisoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate

Base Information

Chemical Name:(S)-tert-butyl 4-(3-(benzyloxy)-4-formylisoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate
CAS No.:1410805-01-4
Molecular Formula:C₂₁H₂₆N₂O₆
Molecular Weight:402.447
Hs Code.:

Synonyms:(S)-tert-butyl 4-(3-(benzyloxy)-4-formylisoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate

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Chemical Property of (S)-tert-butyl 4-(3-(benzyloxy)-4-formylisoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate

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Technology Process of (S)-tert-butyl 4-(3-(benzyloxy)-4-formylisoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate

There total 4 articles about (S)-tert-butyl 4-(3-(benzyloxy)-4-formylisoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate 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%

: 1410805-00-3
(S)-tert-butyl 4-(3-(benzyloxy)-4-(hydroxymethyl)isoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate

: 1410805-01-4
(S)-tert-butyl 4-(3-(benzyloxy)-4-formylisoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: With sulfur trioxide pyridine complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 0 ℃; for 0.583333h; Inert atmosphere;
DOI:10.1021/ol302691j

Reference yield:

: 1410804-99-7
(S)-methyl 3-(benzyloxy)-5-(3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl)isoxazole-4-carboxylate

: 1410805-01-4
(S)-tert-butyl 4-(3-(benzyloxy)-4-formylisoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: diisobutylaluminium hydride / toluene / 0.5 h / -78 °C / Inert atmosphere

2: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.58 h / 0 °C / Inert atmosphere

With sulfur trioxide pyridine complex; diisobutylaluminium hydride; triethylamine; In dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1021/ol302691j

Reference yield:

: 162107-48-4
tert-butyl (R)-4-ethynyl-2,2-dimethyloxazolidine-3-carboxylate

: 1410805-01-4
(S)-tert-butyl 4-(3-(benzyloxy)-4-formylisoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 0.75 h / -78 °C / Inert atmosphere

2.1: potassium hydrogencarbonate; N-chloro-succinimide / ethyl acetate / 72 h / 20 - 48 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 °C / Inert atmosphere

4.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.58 h / 0 °C / Inert atmosphere

With N-chloro-succinimide; sulfur trioxide pyridine complex; diisobutylaluminium hydride; potassium hydrogencarbonate; triethylamine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene;
DOI:10.1021/ol302691j