(1R,2S,3S)-3-(N,N-Dibenzylamino)-1,4-diphenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-butanediol

Base Information

Chemical Name:(1R,2S,3S)-3-(N,N-Dibenzylamino)-1,4-diphenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-butanediol
CAS No.:249923-10-2
Molecular Formula:C₃₈H₄₄N₂O₄
Molecular Weight:592.778
Hs Code.:

Synonyms:(1R,2S,3S)-3-(N,N-Dibenzylamino)-1,4-diphenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-butanediol

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Chemical Property of (1R,2S,3S)-3-(N,N-Dibenzylamino)-1,4-diphenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-butanediol

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Technology Process of (1R,2S,3S)-3-(N,N-Dibenzylamino)-1,4-diphenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-butanediol

There total 7 articles about (1R,2S,3S)-3-(N,N-Dibenzylamino)-1,4-diphenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-butanediol 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: 76.0%

: 249922-96-1
2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (1S,2S)-1-benzoyl-2-dibenzylamino-3-phenyl-propyl ester

: 249923-10-2
(1R,2S,3S)-3-(N,N-Dibenzylamino)-1,4-diphenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-butanediol

: 249923-11-3
(1S,2S,3S)-3-(N,N-Dibenzylamino)-1,4-diphenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-butanediol

Guidance literature:: With sodium tetrahydroborate; manganese(ll) chloride; In methanol; diethyl ether; for 24h; Heating;
DOI:10.1055/s-1999-3575

Reference yield:

: 100-52-7
benzaldehyde

: 247575-73-1
2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (S)-2-dibenzylamino-3-phenyl-propyl ester

: 249923-10-2
(1R,2S,3S)-3-(N,N-Dibenzylamino)-1,4-diphenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-butanediol

: 249923-11-3
(1S,2S,3S)-3-(N,N-Dibenzylamino)-1,4-diphenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-butanediol

Guidance literature:: 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (S)-2-dibenzylamino-3-phenyl-propyl ester; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; hexane; cyclohexane; at -78 ℃;

benzaldehyde; In diethyl ether; hexane; cyclohexane; at -78 - 20 ℃; for 12h;
DOI:10.1055/s-1999-3575

Reference yield:

: 146176-60-5
2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl chloride

: 249923-10-2
(1R,2S,3S)-3-(N,N-Dibenzylamino)-1,4-diphenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-butanediol

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 1 h / Heating

1.2: 81 percent / tetrahydrofuran / 6 h / Heating

2.1: s-BuLi; (-)-sparteine / diethyl ether; cyclohexane; hexane / -78 °C

2.2: diethyl ether; cyclohexane; hexane / 12 h / -78 - 20 °C

3.1: 63 percent / NaBH₄ / methanol; diethyl ether / 24 h / 0 °C

With sodium tetrahydroborate; sec.-butyllithium; sodium hydride; (-)-sparteine; In tetrahydrofuran; methanol; diethyl ether; hexane; cyclohexane; 1.1: Metallation / 1.2: Acylation / 2.1: Metallation / 2.2: Acylation / 3.1: Reduction;
DOI:10.1055/s-1999-3575