(R)-4-((2S,3R)-1-Benzyl-4-oxo-3-phenoxy-azetidin-2-yl)-2-(2-benzyloxycarbonyl-ethyl)-2-methyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(R)-4-((2S,3R)-1-Benzyl-4-oxo-3-phenoxy-azetidin-2-yl)-2-(2-benzyloxycarbonyl-ethyl)-2-methyl-oxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:469886-61-1
Molecular Formula:C₃₅H₄₀N₂O₇
Molecular Weight:600.712
Hs Code.:

Synonyms:(R)-4-((2S,3R)-1-Benzyl-4-oxo-3-phenoxy-azetidin-2-yl)-2-(2-benzyloxycarbonyl-ethyl)-2-methyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of (R)-4-((2S,3R)-1-Benzyl-4-oxo-3-phenoxy-azetidin-2-yl)-2-(2-benzyloxycarbonyl-ethyl)-2-methyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (R)-4-((2S,3R)-1-Benzyl-4-oxo-3-phenoxy-azetidin-2-yl)-2-(2-benzyloxycarbonyl-ethyl)-2-methyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 7 articles about (R)-4-((2S,3R)-1-Benzyl-4-oxo-3-phenoxy-azetidin-2-yl)-2-(2-benzyloxycarbonyl-ethyl)-2-methyl-oxazolidine-3-carboxylic 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: 52.0%

: 701-99-5
Phenoxyacetyl chloride

: 100-46-9
benzylamine

: 469886-51-9
(4S)-2-(2-benzyloxycarbonylethyl)-4-formyl-2-methyloxazolidine-3-carboxylic acid tert-butyl ester

: 469886-61-1
(R)-4-((2S,3R)-1-Benzyl-4-oxo-3-phenoxy-azetidin-2-yl)-2-(2-benzyloxycarbonyl-ethyl)-2-methyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: benzylamine; (4S)-2-(2-benzyloxycarbonylethyl)-4-formyl-2-methyloxazolidine-3-carboxylic acid tert-butyl ester; With 4 A molecular sieve; In dichloromethane; at 20 ℃; for 1h;

Phenoxyacetyl chloride; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 16h; Further stages.;
DOI:10.1021/jo0203239

Reference yield:

: 6939-75-9
benzyl levulinate

: 469886-61-1
(R)-4-((2S,3R)-1-Benzyl-4-oxo-3-phenoxy-azetidin-2-yl)-2-(2-benzyloxycarbonyl-ethyl)-2-methyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 78 percent / isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 12 h / 0 - 20 °C

2.1: 85 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

3.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

3.2: 90 percent / Et₃N / CH₂Cl₂ / 0.25 h / -78 - 20 °C

4.1: molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 20 °C

4.2: 52 percent / Et₃N / CH₂Cl₂ / 16 h / 0 - 20 °C

With oxalyl dichloride; isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation;
DOI:10.1021/jo0203239

Reference yield:

: 123-76-2
levulinic acid

: 469886-61-1
(R)-4-((2S,3R)-1-Benzyl-4-oxo-3-phenoxy-azetidin-2-yl)-2-(2-benzyloxycarbonyl-ethyl)-2-methyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 °C

2.1: 78 percent / isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 12 h / 0 - 20 °C

3.1: 85 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

4.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

4.2: 90 percent / Et₃N / CH₂Cl₂ / 0.25 h / -78 - 20 °C

5.1: molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 20 °C

5.2: 52 percent / Et₃N / CH₂Cl₂ / 16 h / 0 - 20 °C

With dmap; oxalyl dichloride; isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 4.1: Swern oxidation;
DOI:10.1021/jo0203239