2-Oxazolidinone, 3-[(2R)-2-(1-hydroxyethyl)-1-oxo-4-pentenyl]-4-methyl-5-phenyl-, (4R,5S)-

Base Information

• Chemical Name: 2-Oxazolidinone, 3-[(2R)-2-(1-hydroxyethyl)-1-oxo-4-pentenyl]-4-methyl-5-phenyl-, (4R,5S)-
• CAS No.: 393563-08-1
• Molecular Formula: C17H21NO4
• Molecular Weight: 303.358
• Mol file: 393563-08-1.mol

Synonyms:

Chemical Property of 2-Oxazolidinone, 3-[(2R)-2-(1-hydroxyethyl)-1-oxo-4-pentenyl]-4-methyl-5-phenyl-, (4R,5S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Oxazolidinone, 3-[(2R)-2-(1-hydroxyethyl)-1-oxo-4-pentenyl]-4-methyl-5-phenyl-, (4R,5S)-

There total 1 articles about 2-Oxazolidinone, 3-[(2R)-2-(1-hydroxyethyl)-1-oxo-4-pentenyl]-4-methyl-5-phenyl-, (4R,5S)- 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%

(4R,5S)-4-methyl-3-pent-4-enoyl-5-phenyloxazolidin-2-one (96930-18-6) + acetaldehyde (75-07-0,9002-91-9) → (4R,5S)-3[(2R)-2-((1R*)-1-hydroxyethyl)-1-oxo-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone (393563-08-1)

Guidance literature:

(4R,5S)-4-methyl-3-pent-4-enoyl-5-phenyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

acetaldehyde; In dichloromethane; at -78 - 20 ℃; Further stages.;

DOI:10.1021/jo010751z

Reference yield: 92.0%

phenylcarbonochloridothioate (1005-56-7) + (4R,5S)-3[(2R)-2-((1R*)-1-hydroxyethyl)-1-oxo-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone (393563-08-1) → (4R,5S)-3-[(2R)-2((1R*)-1-(phenoxythiocarbonyloxy)ethyl)-1-oxo-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone (393563-09-2)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jo010751z

Reference yield:

(4R,5S)-3[(2R)-2-((1R*)-1-hydroxyethyl)-1-oxo-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone (393563-08-1) → vinburnine (4880-88-0)

Guidance literature:

Multi-step reaction with 20 steps

1.1: 92 percent / DMAP; pyridine / CH₂Cl₂ / 3 h / 20 °C

2.1: 76 percent / Bu₃SnH; AIBN / toluene / 12 h / 75 °C

3.1: 100 percent / LiOH*H₂O; H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 °C

4.1: 0.023 g / LiAlH₄ / diethyl ether / 0 - 20 °C

5.1: 86 percent / DCC; DMAP / CH₂Cl₂ / 1 h / 0 °C

6.1: disiamylborane / tetrahydrofuran / 0 - 20 °C

6.2: 74 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0.33 h / 10 - 20 °C

7.1: 89 percent / pyridine / 12 h / 0 - 20 °C

8.1: 88 percent / MsN₃; Et₃N / acetonitrile / 10 h / 20 °C

9.1: 87 percent / Rh₂(OAc)4 / CH₂Cl₂ / 14 h / Heating

10.1: 84 percent / NaCl; H₂O / dimethylsulfoxide / 12 h / 110 °C

11.1: 93 percent / Bu₄NF / tetrahydrofuran / 0.67 h / 20 °C

12.1: 98 percent / Jones reagent / acetone / 0 °C

13.1: DCC / CH₂Cl₂ / 1 h / 0 °C

13.2: 67 percent / CH₂Cl₂ / 15 h / 20 °C

14.1: 92 percent / LiBH₄ / tetrahydrofuran; methanol / 48 h / 20 °C

15.1: 92 percent / imidazole / dimethylformamide / 16 h / -20 - 20 °C

16.1: Et₃N; Py*SO₃ / dimethylsulfoxide / 60 h / 20 °C

16.2: 18.7 mg / TFA / CH₂Cl₂ / 16 h / -42 - 20 °C

17.1: 96 percent / Me₃SiCl / methanol / 3 h / 0 - 20 °C

18.1: 30 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

19.1: Py*SO₃; Et₃N / dimethylsulfoxide / 20 h / 20 °C

20.1: 2 mg / NMMO; TPAP; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 20 °C

With pyridine; 1H-imidazole; dmap; lithium hydroxide; lithium aluminium tetrahydride; lithium borohydride; chloro-trimethyl-silane; jones reagent; tetrapropylammonium perruthennate; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; tri-n-butyl-tin hydride; sulfur trioxide pyridine complex; bis-(1,2-dimethylpropyl)borane; 4-methylmorpholine N-oxide; triethylamine; Methanesulfonyl azide; dicyclohexyl-carbodiimide; sodium chloride; dirhodium tetraacetate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 12.1: Jones oxidation / 16.2: Pictet-Spengler cyclization;

DOI:10.1021/jo010751z

upstream raw materials:

(4R,5S)-4-methyl-3-pent-4-enoyl-5-phenyloxazolidin-2-one

acetaldehyde

Downstream raw materials:

(4R,5S)-3-[(2R)-2((1R*)-1-(phenoxythiocarbonyloxy)ethyl)-1-oxo-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone

(4R,5S)-3-[(2S)-1-oxo-2-ethyl-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone

vinburnine

(4S)-4-[3-(tert-butyldiphenylsilyloxypropyl)]-4-ethyldihydro-2(3H)-furanone