(3R,4S,5R)-ethyl 2-benzhydryl-4-formyl-3,5-dimethylisoxazolidine-3-carboxylate

Base Information

Chemical Name:(3R,4S,5R)-ethyl 2-benzhydryl-4-formyl-3,5-dimethylisoxazolidine-3-carboxylate
CAS No.:1416476-05-5
Molecular Formula:C₂₂H₂₅NO₄
Molecular Weight:367.445
Hs Code.:

Synonyms:(3R,4S,5R)-ethyl 2-benzhydryl-4-formyl-3,5-dimethylisoxazolidine-3-carboxylate

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Chemical Property of (3R,4S,5R)-ethyl 2-benzhydryl-4-formyl-3,5-dimethylisoxazolidine-3-carboxylate

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Technology Process of (3R,4S,5R)-ethyl 2-benzhydryl-4-formyl-3,5-dimethylisoxazolidine-3-carboxylate

There total 10 articles about (3R,4S,5R)-ethyl 2-benzhydryl-4-formyl-3,5-dimethylisoxazolidine-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:

: 123-73-9,4170-30-3
trans-Crotonaldehyde

: 1416475-89-2
(E)-N-(1-ethoxy-1-oxopropan-2-ylidene)-1,1-diphenylmethanamine oxide

: 1416476-05-5
(3R,4S,5R)-ethyl 2-benzhydryl-4-formyl-3,5-dimethylisoxazolidine-3-carboxylate

: (3S,4R,5S)-ethyl 2-benzhydryl-4-formyl-3,5-dimethylisoxazolidine-3-carboxylate

Guidance literature:: (E)-N-(1-ethoxy-1-oxopropan-2-ylidene)-1,1-diphenylmethanamine oxide; With (2S,2'S)-N,N'-((S)-1,1'-binaphthyl-2,2'-diyl)bis(2-amino-3-phenylpropanamide); water; In nitromethane; at 4 ℃; for 0.166667h; Inert atmosphere;

trans-Crotonaldehyde; With trifluorormethanesulfonic acid; In nitromethane; for 72h; Overall yield = 85 %; Overall yield = 78.6 mg; enantioselective reaction; Inert atmosphere;
DOI:10.1016/j.tetasy.2012.11.010

Reference yield:

: 91-00-9
Benzhydrylamine

: 1416476-05-5
(3R,4S,5R)-ethyl 2-benzhydryl-4-formyl-3,5-dimethylisoxazolidine-3-carboxylate

: (3S,4R,5S)-ethyl 2-benzhydryl-4-formyl-3,5-dimethylisoxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / acetonitrile / 72 h / 20 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

2.2: 0.33 h / Inert atmosphere

3.1: sodium acetate trihydrate / methanol / 20 °C / Inert atmosphere

4.1: (2S,2'S)-N,N'-((S)-1,1'-binaphthyl-2,2'-diyl)bis(2-amino-3-phenylpropanamide); water / nitromethane / 0.17 h / 4 °C / Inert atmosphere

4.2: 72 h / Inert atmosphere

With (2S,2'S)-N,N'-((S)-1,1'-binaphthyl-2,2'-diyl)bis(2-amino-3-phenylpropanamide); water; sodium acetate trihydrate; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; nitromethane; dichloromethane; acetonitrile;
DOI:10.1016/j.tetasy.2012.11.010

Reference yield:

: 146495-24-1
N-(diphenylmethylene)aminoacetonitrile

: 1416476-05-5
(3R,4S,5R)-ethyl 2-benzhydryl-4-formyl-3,5-dimethylisoxazolidine-3-carboxylate

: (3S,4R,5S)-ethyl 2-benzhydryl-4-formyl-3,5-dimethylisoxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

1.2: 0.33 h / Inert atmosphere

2.1: sodium acetate trihydrate / methanol / 20 °C / Inert atmosphere

3.1: (2S,2'S)-N,N'-((S)-1,1'-binaphthyl-2,2'-diyl)bis(2-amino-3-phenylpropanamide); water / nitromethane / 0.17 h / 4 °C / Inert atmosphere

3.2: 72 h / Inert atmosphere

With (2S,2'S)-N,N'-((S)-1,1'-binaphthyl-2,2'-diyl)bis(2-amino-3-phenylpropanamide); water; sodium acetate trihydrate; 3-chloro-benzenecarboperoxoic acid; In methanol; nitromethane; dichloromethane;
DOI:10.1016/j.tetasy.2012.11.010