(4R,5S)-5-azido-4-(4-methoxyphenyl)-6-oxo-6-[(4S)-(2-oxo-4-phenyloxazolidin-3-yl)]hexanoic acid tert-butyl ester

Base Information

Chemical Name:(4R,5S)-5-azido-4-(4-methoxyphenyl)-6-oxo-6-[(4S)-(2-oxo-4-phenyloxazolidin-3-yl)]hexanoic acid tert-butyl ester
CAS No.:600708-97-2
Molecular Formula:C₂₆H₃₀N₄O₆
Molecular Weight:494.547
Hs Code.:

Synonyms:(4R,5S)-5-azido-4-(4-methoxyphenyl)-6-oxo-6-[(4S)-(2-oxo-4-phenyloxazolidin-3-yl)]hexanoic acid tert-butyl ester

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Chemical Property of (4R,5S)-5-azido-4-(4-methoxyphenyl)-6-oxo-6-[(4S)-(2-oxo-4-phenyloxazolidin-3-yl)]hexanoic acid tert-butyl ester

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Technology Process of (4R,5S)-5-azido-4-(4-methoxyphenyl)-6-oxo-6-[(4S)-(2-oxo-4-phenyloxazolidin-3-yl)]hexanoic acid tert-butyl ester

There total 5 articles about (4R,5S)-5-azido-4-(4-methoxyphenyl)-6-oxo-6-[(4S)-(2-oxo-4-phenyloxazolidin-3-yl)]hexanoic acid tert-butyl ester 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:

: (R)-5-Bromo-4-(4-methoxy-phenyl)-6-oxo-6-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-hexanoic acid tert-butyl ester

: 600708-97-2
(4R,5S)-5-azido-4-(4-methoxyphenyl)-6-oxo-6-[(4S)-(2-oxo-4-phenyloxazolidin-3-yl)]hexanoic acid tert-butyl ester

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; for 4h;
DOI:10.1021/jo0340152

Reference yield:

: 59854-12-5
tert-butyl 4-hydroxybutyrate

: 600708-97-2
(4R,5S)-5-azido-4-(4-methoxyphenyl)-6-oxo-6-[(4S)-(2-oxo-4-phenyloxazolidin-3-yl)]hexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.25 h / -75 °C

2.1: 5.7 g / LiCl; diisopropylethylamine / acetonitrile / 24 h / 20 °C

3.1: CuBr*Me₂S / tetrahydrofuran; various solvent(s) / 0.5 h / -45 - -10 °C

3.2: tetrahydrofuran; various solvent(s) / 0.33 h / -15 - -10 °C

3.3: NBS / tetrahydrofuran; various solvent(s) / 1 h / -78 °C

4.1: 850 mg / NaN₃ / dimethylformamide / 4 h / 20 °C

With sodium azide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Swern oxidation / 3.2: Michael addition;
DOI:10.1021/jo0340152

Reference yield:

: 15026-17-2
succinic acid mono-tert-butyl ester

: 600708-97-2
(4R,5S)-5-azido-4-(4-methoxyphenyl)-6-oxo-6-[(4S)-(2-oxo-4-phenyloxazolidin-3-yl)]hexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 74 percent / BH₃*Me₂S / tetrahydrofuran / 24 h / 20 °C

2.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.25 h / -75 °C

3.1: 5.7 g / LiCl; diisopropylethylamine / acetonitrile / 24 h / 20 °C

4.1: CuBr*Me₂S / tetrahydrofuran; various solvent(s) / 0.5 h / -45 - -10 °C

4.2: tetrahydrofuran; various solvent(s) / 0.33 h / -15 - -10 °C

4.3: NBS / tetrahydrofuran; various solvent(s) / 1 h / -78 °C

5.1: 850 mg / NaN₃ / dimethylformamide / 4 h / 20 °C

With sodium azide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; dimethylsulfide borane complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2.1: Swern oxidation / 4.2: Michael addition;
DOI:10.1021/jo0340152