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1412967-14-6

1412967-14-6

Identification

Synonyms:(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one

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Relevant articles and documentsAll total 2 Articles be found

Formal Synthesis of Ezetimibe Using a Proline-mediated, Asymmetric, Three-component Mannich Reaction

Shimasaki, Yasuharu,Koshino, Seitaro,Hayashi, Yujiro

, p. 30 - 32 (2016)

The formal total synthesis of ezetimibe was accomplished using a proline-mediated, asymmetric, three-component Mannich reaction as the key step. The two stereogenic centers on the β-lactam skeleton of ezetimibe were controlled by the syn-selective asymmetric Mannich reaction, followed by isomerization.

Synthesis and Evaluation of 2-Azetidinone and 1H-Pyrrole-2,5-dione Derivatives as Cholesterol Absorption Inhibitors for Reducing Inflammation Response and Oxidative Stress

Xia, Yineng,Zhu, Lijuan,Yuan, Xinrui,Wang, Yubin

, (2019/01/10)

Excess lipid accumulation can initiate the development and progression of atherosclerotic lesions, thus eventually leading to cardiovascular disease. Lipid-lowering medication therapy is one of the cornerstones of cardiovascular disease therapy. On the basis of the cholesterol absorption inhibitor ezetimibe, we successfully synthesized seven 2-azetidinone derivatives and eighteen 1H-pyrrole-2,5-dione derivatives. Most of the new compounds significantly inhibited cholesterol uptake in vitro. In addition, one of the most active inhibitors, 3-(4-fluorophenyl)-1-[(3S)-3-hydroxy-3-(4-hydroxyphenyl)propyl]-4-(4-hydroxyphenyl)-1H-pyrrole-2,5-dione (14q), showed no cytotoxicity in L02 and HEK293T cell lines. Further evaluation indicated that 14q inhibited considerably the amount of TNF-α, ROS, MDA, and LDH in vitro. Therefore, 14q might be a novel cholesterol absorption inhibitor.

Process route upstream and downstream products

Process route

(3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone
204589-82-2

(3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one
1412967-14-6

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one

Conditions
Conditions Yield
With dimethylsulfide borane complex; In tetrahydrofuran; at -10 ℃; for 8h;
61%
(3R,4S)-3-allyl-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)azetidin-2-one

(3R,4S)-3-allyl-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)azetidin-2-one

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one
1412967-14-6

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one

Conditions
Conditions Yield
(3R,4S)-3-allyl-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)azetidin-2-one; With 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;
With sodium perborate tetrahydrate; In water; at 0 - 20 ℃; for 2h; Inert atmosphere;
80%
methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate
204589-80-0

methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one
1412967-14-6

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: lithium hydroxide / water / 1 h / 20 °C
2: dimethylsulfide borane complex / tetrahydrofuran / 8 h / -10 °C
With dimethylsulfide borane complex; lithium hydroxide; In tetrahydrofuran; water;
(S)-2-((S)-(4-(benzyloxy)phenyl)((4-fluorophenyl)amino)methyl)pent-4-enoicacid

(S)-2-((S)-(4-(benzyloxy)phenyl)((4-fluorophenyl)amino)methyl)pent-4-enoicacid

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one
1412967-14-6

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: triethylamine; thionyl chloride / dichloromethane / 3 h / 20 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere
3.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
3.2: 2 h / 0 - 20 °C / Inert atmosphere
With thionyl chloride; potassium tert-butylate; 9-borabicyclo[3.3.1]nonane; triethylamine; In tetrahydrofuran; dichloromethane;
(S)-2-((S)-(4-(benzyloxy)phenyl)((4-fluorophenyl)amino)methyl)pent-4-enal

(S)-2-((S)-(4-(benzyloxy)phenyl)((4-fluorophenyl)amino)methyl)pent-4-enal

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one
1412967-14-6

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: sodium chlorite; sodium dihydrogen phosphate; N,N-dimethyl-aniline / water; tert-butyl alcohol / 0.67 h / 0 °C / Inert atmosphere
2.1: triethylamine; thionyl chloride / dichloromethane / 3 h / 20 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere
4.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
4.2: 2 h / 0 - 20 °C / Inert atmosphere
With sodium chlorite; thionyl chloride; sodium dihydrogen phosphate; potassium tert-butylate; N,N-dimethyl-aniline; 9-borabicyclo[3.3.1]nonane; triethylamine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
(3S,4S)-3-allyl-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)azetidin-2-one

(3S,4S)-3-allyl-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)azetidin-2-one

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one
1412967-14-6

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere
2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
2.2: 2 h / 0 - 20 °C / Inert atmosphere
With potassium tert-butylate; 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran;
(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one
1412967-14-6

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one

(3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone
204589-82-2

(3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
Conditions Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In dichloromethane; water; at 20 ℃; for 6h; Inert atmosphere;
77%
(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one
1412967-14-6

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: sodium hydrogencarbonate; sodium hypochlorite; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / Difluoromethane / 25 °C / Cooling with ice
2.1: (R)-1,1'-Bi-2-naphthol / titanium(IV) isopropylate / diethyl ether; tetrahydrofuran / 1.5 h / 0 - 25 °C
2.2: -20 - 25 °C
2.3: 0 °C
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; (R)-1,1'-Bi-2-naphthol; sodium hydrogencarbonate; potassium bromide; titanium(IV) isopropylate; In tetrahydrofuran; diethyl ether; Difluoromethane;
(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one
1412967-14-6

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]propyl 4-methylbenzenesulfonate

3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]propyl 4-methylbenzenesulfonate

Conditions
Conditions Yield
With dmap; triethylamine; In dichloromethane; at 20 ℃; for 6h;
(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one
1412967-14-6

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one

C<sub>35</sub>H<sub>37</sub>FN<sub>2</sub>O<sub>4</sub>S

C35H37FN2O4S

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: triethylamine; dmap / dichloromethane / 6 h / 20 °C
2: potassium carbonate / acetonitrile / 12 h / 90 °C
With dmap; potassium carbonate; triethylamine; In dichloromethane; acetonitrile;

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