(R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine

Base Information

Chemical Name:(R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine
CAS No.:271260-96-9
Molecular Formula:C₂₁H₃₃NO₃
Molecular Weight:347.498
Hs Code.:

Synonyms:(R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine

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Chemical Property of (R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine

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Technology Process of (R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine

There total 5 articles about (R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine 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: 77.0%

: 576-83-0
2,4,6-trimethylphenyl bromide

: 115378-31-9
tert-butyl (4R)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate

: 271260-96-9
(R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine

Guidance literature:: tert-butyl (4R)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate; With 9-borabicyclo[3.3.1]nonane dimer; In toluene; at 80 - 85 ℃;

2,4,6-trimethylphenyl bromide; With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide; In toluene; at 90 ℃; Further stages.;
DOI:10.1021/ol005645i

Reference yield: 69.0%

: 576-83-0
2,4,6-trimethylphenyl bromide

: 102308-32-7
(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 18107-18-1
diazomethyl-trimethyl-silane

: 271260-96-9
(R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine

Guidance literature:: (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester; diazomethyl-trimethyl-silane; With triphenylphosphine; isopropyl alcohol; copper(l) chloride; In tetrahydrofuran; at 60 ℃;

With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; toluene; at 80 ℃;

2,4,6-trimethylphenyl bromide; With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; toluene; at 90 ℃; Further stages.;
DOI:10.1021/ja0733235

Reference yield:

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

: 271260-96-9
(R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2.1 g / NaHCO₃ / methanol; ethyl acetate; H₂O / biphasic

2.1: 46 percent / Pseudomonas cepecia (Amano PS-30) lipase / CH₂Cl₂ / 20 °C / Enzymatic reaction

3.1: BF₃*Et₂O / acetone / -20 - 20 °C

4.1: 9-BBN / toluene / 80 - 85 °C

4.2: 77 percent / aq. NaOH; Pd(PPh₃)4; TBAI / toluene / 90 °C

With 9-borabicyclo[3.3.1]nonane dimer; Pseudomonas cepecia (Amano PS-30) lipase; boron trifluoride diethyl etherate; sodium hydrogencarbonate; In methanol; dichloromethane; water; ethyl acetate; acetone; toluene; 1.1: Acylation / 2.1: Acetylation / 3.1: Condensation / 4.1: hydroboration / 4.2: Suzuki cross-coupling;
DOI:10.1021/ol005645i