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

Base Information

Chemical Name:(1S,2R,3R)-3-(N,N-Dibenzylamino)-1-phenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-pentanediol
CAS No.:249923-08-8
Molecular Formula:C₃₃H₄₂N₂O₄
Molecular Weight:530.707
Hs Code.:

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

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

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

There total 5 articles about (1S,2R,3R)-3-(N,N-Dibenzylamino)-1-phenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-pentanediol 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: 87.0%

: 249922-84-7
2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (1R,2R)-1-benzoyl-2-dibenzylamino-butyl ester

: 249923-09-9
(1R,2R,3R)-3-(N,N-Dibenzylamino)-1-phenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-pentanediol

: 249923-08-8
(1S,2R,3R)-3-(N,N-Dibenzylamino)-1-phenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-pentanediol

Guidance literature:: With zinc(II) tetrahydroborate; In diethyl ether; at 20 ℃; for 3h;
DOI:10.1055/s-1999-3575

Reference yield:

: 100-52-7
benzaldehyde

: 247576-09-6
2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (R)-2-dibenzylamino-butyl ester

: 249923-09-9
(1R,2R,3R)-3-(N,N-Dibenzylamino)-1-phenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-pentanediol

: 249923-08-8
(1S,2R,3R)-3-(N,N-Dibenzylamino)-1-phenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-pentanediol

Guidance literature:: 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (R)-2-dibenzylamino-butyl ester; With sec.-butyllithium; (-)-sparteine; 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:

: 100-39-0
benzyl bromide

: 249923-08-8
(1S,2R,3R)-3-(N,N-Dibenzylamino)-1-phenyl-2-O-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl)-1,2-pentanediol

Guidance literature:: Multi-step reaction with 4 steps

1.1: K₂CO₃; NaOH / aq. methanol / 0.5 h / Heating

1.2: 98 percent / aq. methanol / 6 h / Heating

2.1: NaH / tetrahydrofuran / 1 h / Heating

2.2: 79 percent / tetrahydrofuran / 6 h / Heating

3.1: s-BuLi; TMEDA / diethyl ether; cyclohexane; hexane / -78 °C

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

4.1: 87 percent / Zn(BH₄)2 / diethyl ether / 3 h / 20 °C

With sodium hydroxide; zinc(II) tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; cyclohexane; 1.1: Metallation / 1.2: Alkylation / 2.1: Metallation / 2.2: Acylation / 3.1: Metallation / 3.2: Acylation / 4.1: Reduction;
DOI:10.1055/s-1999-3575