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【结 构 式】

【分子编号】20656

【品名】(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-2-azetidinone

【CA登记号】

【 分 子 式 】C31H25F2NO3

【 分 子 量 】497.5412464

【元素组成】C 74.84% H 5.06% F 7.64% N 2.82% O 9.65%

与该中间体有关的原料药合成路线共 8 条

合成路线1

该中间体在本合成路线中的序号:(VII)

Treatment of acid chloride (I) with tributylamine generated the corresponding ketene, which was cyclocondensed to imine (II) to produce the racemic trans b-lactam (III). Resolution of (III) into enantiomers was then achieved by preparative HPLC on a Chiralcel OD column. Subsequent saponification of the desired enantiomer with methanolic LiOH afforded acid (IV), which was converted to acid chloride (V) upon treatment with oxalyl chloride. Further Pd-mediated coupling of (V) with the arylzinc reagent (VI) provided ketone (VII). Then, carbonyl reduction with BH3-Me2S, followed by chromatographic separation of the isomers furnished alcohol (VIII), which was finally deprotected by hydrogenolysis over Pd/C to afford the target phenol.

1 Afonso, A.; Davis, H.R. Jr.; Huynh, T.; Yumibe, N.; Clader, J.W.; Burnett, D.A.; Rosenblum, S.B.; Discovery of 1-(4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235): A designed, potent, orally active inhibitor of cholesterol absorption. J Med Chem 1998, 41, 6, 973.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 20650 methyl 5-chloro-5-oxopentanoate; methyl-4-chloroformylbutyrate 1501-26-4 C6H9ClO3 详情 详情
(II) 20651 N-[(E)-[4-(benzyloxy)phenyl]methylidene]-4-fluoroaniline; N-[(E)-[4-(benzyloxy)phenyl]methylidene]-N-(4-fluorophenyl)amine C20H16FNO 详情 详情
(III) 20652 (rac)-methyl 3-[(2S*,3R*)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidinyl]propanoate C26H24FNO4 详情 详情
(IV) 20653 3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidinyl]propionic acid C25H22FNO4 详情 详情
(V) 20654 3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidinyl]propanoyl chloride C25H21ClFNO3 详情 详情
(VI) 20655 bromo(4-fluorophenyl)zinc C6H4BrFZn 详情 详情
(VII) 20656 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-2-azetidinone C31H25F2NO3 详情 详情
(VIII) 20657 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-2-azetidinone C31H27F2NO3 详情 详情

合成路线2

该中间体在本合成路线中的序号:trans-(X)

1) The cyclization of 4(S)-hydroxytetrahydrofuran-2-one (I) with the benzylideneimine derivative (II) by means of LDA gives the trans-azetidinone (III), which is separated from its cis-isomer by crystallization. The oxidation of (III) with NaIO4 in acetonitrile yields the carbaldehyde (IV), which is condensed with the silylated enol ether (V), prepared from 4'-fluoroacetophenone (VI), Li and TMSCl, to afford compound (VII). The dehydration of (VII) by means of TsOH gives the enone (VIII), which is hydrogenated and debenzylated with H2 over Pd/C in ethanol, providing the saturated ketone (IX). Finally, this compound is enantioselectively reduced with borane and the chiral catalyst (R)-1-methyl-3,3-diphenylperhydropyrrolo[1,2-c][1,3,2]oxaazaborole (CBS). 2) Alternatively, the reduction of enone (VIII) with H2 over RhCl(PPh3)3 in dichloromethane gives the benzylated saturated ketone (X), which is enantioselectively reduced with borane and CBS, yielding the benzylated alcohol (XI). Finally, this compound is debenzylated with H2 over Pd/C in ethanol.

1 Wu, G.-Z.; Chen, X.; Wong, Y.-S.; Schumacher, D.P.; Steinman, M.; 3-Hydroxy gamma-lactone based enantioselective synthesis of azetidinones. US 5886171 .
2 Castañer, R.M.; Sorbera, L.A.; Castañer, J.; Ezetimibe. Drugs Fut 2000, 25, 7, 679.
3 Wu, G.Z.; Chen, X.; Ding, Z.; Wong, Y.S.; A novel one-step diastereo- and enantioselective formation of trans-azetidinones and its application to the total synthesis of cholesterol absorption inhibitors. J Org Chem 1999, 64, 10, 3714.
4 Steinman, M.; Schumacher, D.P.; Chen, X.; Wu, G.-Z.; Wong, Y.-S. (Schering Corp.); 3-Hydroxy gamma-lactone based enantioselective synthesis of azetidinones. WO 9745406 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
trans-(X) 20656 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-2-azetidinone C31H25F2NO3 详情 详情
trans-(III) 37682 (3S,4S)-4-[4-(benzyloxy)phenyl]-3-[(1S)-1,2-dihydroxyethyl]-1-(4-fluorophenyl)-2-azetidinone C24H22FNO4 详情 详情
trans-(IV) 37683 (2S,3S)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxo-3-azetidinecarbaldehyde C23H18FNO3 详情 详情
trans-(VIII) 37686 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[(E)-3-(4-fluorophenyl)-3-oxo-1-propenyl]-2-azetidinone C31H23F2NO3 详情 详情
trans-(VII) 37687 (3S,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[(1R)-3-(4-fluorophenyl)-1-hydroxy-3-oxopropyl]-2-azetidinone C31H25F2NO4 详情 详情
trans-(IX) 37688 (3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-4-(4-hydroxyphenyl)-2-azetidinone C24H19F2NO3 详情 详情
(I) 37681 (4S)-4-hydroxydihydro-2(3H)-furanone; (S)-3-Hydroxy-gamma-butyrolactone 7331-52-4 C4H6O3 详情 详情
(II) 37689 N-[(Z)-[4-(benzyloxy)phenyl]methylidene]-4-fluoroaniline; N-[(Z)-[4-(benzyloxy)phenyl]methylidene]-N-(4-fluorophenyl)amine C20H16FNO 详情 详情
(V) 37685 [[1-(4-fluorophenyl)vinyl]oxy](trimethyl)silane; 1-(4-fluorophenyl)vinyl trimethylsilyl ether C11H15FOSi 详情 详情
(VI) 37684 1-(4-fluorophenyl)-1-ethanone 403-42-9 C8H7FO 详情 详情
(XI) 20657 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-2-azetidinone C31H27F2NO3 详情 详情

合成路线3

该中间体在本合成路线中的序号:(XX)

3) The reaction of 4-hydroxybenzaldehyde (XII) with benzyl bromide and K2CO3 in acetone gives 4-(benzyloxy)benzaldehyde (XIII), which is condensed with 4-fluoroaniline (XIV) in isopropanol, yielding the imine (II). Cyclization of (II) with methyl 4-(chloroformyl)butyrate (XV) by means of tributylamine in toluene affords the trans-azetidinone (XVI), which is hydrolyzed with LiOH in THF/water to provide the propionic acid derivative (XVII). The reaction of (XVII) with oxalyl chloride in dichloromethane gives the corresponding acyl chloride (XVIII), which is condensed with 4-fluorophenylmagnesium bromide (XIX) by means of ZnCl2 and Pd(PPh3)4 in THF to yield a racemic mixture of saturated trans-azetidinones that was resolved by chiral HPLC to the trans-(3R,4S)-enantiomer (XX). The enantioselective reduction of (XX) with BH3 and the chiral oxaborole catalyst CBS gives the benzylated alcohol (XI), which is finally debenzylated as before with H2 over Pd/C in ethanol.

1 Vaccaro, W.D.; Sher, R.; Davis, H.R. Jr.; 2-Azetidinone cholesterol absorption inhibitors: Increased potency by substitution of the C-4 phenyl ring. Bioorg Med Chem 1998, 6, 9, 1429.
2 Rosenblum, S.B.; Dugar, S.; Burnett, D.A.; Clader, J.W.; McKittrick, B.A. (Schering Corp.); Hydroxy-substd. azetidinone cpds. useful as hypocholesterolemic agents. EP 0720599; JP 1996509989; US 5631365; WO 9508532 .
3 Castañer, R.M.; Sorbera, L.A.; Castañer, J.; Ezetimibe. Drugs Fut 2000, 25, 7, 679.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
trans-(XVI) 20652 (rac)-methyl 3-[(2S*,3R*)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidinyl]propanoate C26H24FNO4 详情 详情
trans-(XVII) 20653 3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidinyl]propionic acid C25H22FNO4 详情 详情
trans-(XVIII) 20654 3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidinyl]propanoyl chloride C25H21ClFNO3 详情 详情
(II) 37689 N-[(Z)-[4-(benzyloxy)phenyl]methylidene]-4-fluoroaniline; N-[(Z)-[4-(benzyloxy)phenyl]methylidene]-N-(4-fluorophenyl)amine C20H16FNO 详情 详情
(XI) 20657 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-2-azetidinone C31H27F2NO3 详情 详情
(XII) 13433 4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde 123-08-0 C7H6O2 详情 详情
(XIII) 29179 4-(Benzyloxy)benzaldehyde 4397-53-9 C14H12O2 详情 详情
(XIV) 37690 4-fluorophenylamine; 4-fluoroaniline 371-40-4 C6H6FN 详情 详情
(XV) 20650 methyl 5-chloro-5-oxopentanoate; methyl-4-chloroformylbutyrate 1501-26-4 C6H9ClO3 详情 详情
(XIX) 13643 4-fluorophenyl magnesium bromide;Bromo(4-fluorophenyl)magnesium;bromo(p-fluorophenyl)Magnesium;p-Fluorophenylmagnesium bromide 352-13-6 C6H4BrFMg 详情 详情
(XX) 20656 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-2-azetidinone C31H25F2NO3 详情 详情

合成路线4

该中间体在本合成路线中的序号:(XX)

4) The reaction of methyl 4-(chloroformyl)butyrate (XV) with the chiral oxazolidinone (XXI) by means of DMAP and TEA in dichloromethane gives the acylated oxazolidinone (XXII), which is cyclized with the benzylideneimine (II) by means of TiCl4, titanium isopropoxide and TBAF in dichloromethane, yielding trans-(3R,4S)-azetidinone (XXIII). This chiral compound (XXIII) is worked up to give ezetimibe by the same reaction sequence used for its racemic analogue (XVI) but without optical resolution. 5) Racemic trans-azetidinone (XVI) can be submitted to chiral chromatography (Chiracel OD column), microbial or enzymatic subtractive resolution to provide the trans-(3R,4S)-azetidinone (XXIII) or direct microbial or enzymatic hydrolytic resolution to directly provide the trans-(3R,4S)-azetidinone-propionic acid (XXIV), the compound also obtained by hydrolysis of (XXIII) with LiOH. This (3R,4S)-free acid (XXIV) is treated with oxalyl chloride giving the (3R,4S)-acyl chloride (XXV), which by condensation with 4-fluorophenylmagnesium bromide (XIX) yields the (3R,4S)-azetidinone (XX). Reduction of (XX) with borane-dimethylsulfide complex in THF affords an equal mixture of diasteromeric alcohols that was submitted to chiral chromatography on a Chiracel OD column providing the benzylated (3'S)-alcohol (XI).

1 Afonso, A.; Davis, H.R. Jr.; Huynh, T.; Yumibe, N.; Clader, J.W.; Burnett, D.A.; Rosenblum, S.B.; Discovery of 1-(4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235): A designed, potent, orally active inhibitor of cholesterol absorption. J Med Chem 1998, 41, 6, 973.
2 Castañer, R.M.; Sorbera, L.A.; Castañer, J.; Ezetimibe. Drugs Fut 2000, 25, 7, 679.
3 Homann, M.J.; Morgan, W.B. (Schering Corp.); Resolution of trans-2-(alkoxycarbonylethyl)-lactams useful in the synthesis of 1-(4-fluoro-phenyl)-3(R)-[(S)-hydroxy-3-(4-fluorophenyl)-propyl]-4(S)-(4-hydroxyphenyl)-2-azetidinone. US 5919672 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
trans-(XVI),(XX 20652 (rac)-methyl 3-[(2S*,3R*)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidinyl]propanoate C26H24FNO4 详情 详情
(II) 37689 N-[(Z)-[4-(benzyloxy)phenyl]methylidene]-4-fluoroaniline; N-[(Z)-[4-(benzyloxy)phenyl]methylidene]-N-(4-fluorophenyl)amine C20H16FNO 详情 详情
(XI) 20657 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-2-azetidinone C31H27F2NO3 详情 详情
(XV) 20650 methyl 5-chloro-5-oxopentanoate; methyl-4-chloroformylbutyrate 1501-26-4 C6H9ClO3 详情 详情
(XIX) 13643 4-fluorophenyl magnesium bromide;Bromo(4-fluorophenyl)magnesium;bromo(p-fluorophenyl)Magnesium;p-Fluorophenylmagnesium bromide 352-13-6 C6H4BrFMg 详情 详情
(XX) 20656 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-2-azetidinone C31H25F2NO3 详情 详情
(XXI) 12173 (4S)-4-Phenyl-1,3-oxazolan-2-one; (4S)-4-Phenyl-2-oxazolidinone; (S)-(+)-4-Phenyl-2-oxazolidinone 99395-88-7 C9H9NO2 详情 详情
(XXII) 37691 methyl 5-oxo-5-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]pentanoate C15H17NO5 详情 详情
(XXIII) 65066 methyl 3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidinyl]propanoate C26H24FNO4 详情 详情
(XXIV) 20653 3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidinyl]propionic acid C25H22FNO4 详情 详情
(XXV) 20654 3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidinyl]propanoyl chloride C25H21ClFNO3 详情 详情

合成路线5

该中间体在本合成路线中的序号:(XX)

6) The reaction of 5-(4-fluorophenyl)-4-pentenoic acid (XXVI) with oxalyl chloride gives the acyl chloride (XXVII), which is condensed with the chiral oxazolidinone (XXI) by means of DMAP and DIEA in dichloromethane, yielding the acyloxazolidinone (XXVIII). Condensation of (XXVIII) with the benzylideneimine (II) by means of TiCl4 affords adduct (XXIX), which is cyclized to the chiral azetidinone (XXX). The oxidation of the double bond of (XXX) with benzoquinone and HClO4 catalyzed by Pd(OAc)2 in acetonitrile/water provides the previously reported trans-(3R,4S)-azetidinone (XX), which is worked up to give azetimibe as described before.

1 Castañer, R.M.; Sorbera, L.A.; Castañer, J.; Ezetimibe. Drugs Fut 2000, 25, 7, 679.
2 Shankar, B.B. (Schering Corp.); Process for preparing 1-(4-fluorophenyl)-3(R)-(3(S)-hydroxy-3-([phenyl or 4-fluorophenyl])-propyl)-4(S)-(4-hydroxyphenyl)-2-azetidinone. US 5856473; WO 9716424 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(II) 37689 N-[(Z)-[4-(benzyloxy)phenyl]methylidene]-4-fluoroaniline; N-[(Z)-[4-(benzyloxy)phenyl]methylidene]-N-(4-fluorophenyl)amine C20H16FNO 详情 详情
(XX) 20656 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-2-azetidinone C31H25F2NO3 详情 详情
(XXI) 12173 (4S)-4-Phenyl-1,3-oxazolan-2-one; (4S)-4-Phenyl-2-oxazolidinone; (S)-(+)-4-Phenyl-2-oxazolidinone 99395-88-7 C9H9NO2 详情 详情
(XXVI) 37692 (E)-5-(4-fluorophenyl)-4-pentenoic acid 190595-67-6 C11H11FO2 详情 详情
(XXVII) 37693 (E)-5-(4-fluorophenyl)-4-pentenoyl chloride C11H10ClFO 详情 详情
(XXVIII) 37694 (4S)-3-[(E)-5-(4-fluorophenyl)-4-pentenoyl]-4-phenyl-1,3-oxazolidin-2-one C20H18FNO3 详情 详情
(XXIX) 37695 (4S)-3-[(2R,4E)-2-[(S)-[4-(benzyloxy)phenyl](4-fluoroanilino)methyl]-5-(4-fluorophenyl)-4-pentenoyl]-4-phenyl-1,3-oxazolidin-2-one C40H34F2N2O4 详情 详情
(XXX) 37696 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[(E)-3-(4-fluorophenyl)-2-propenyl]-2-azetidinone C31H25F2NO2 详情 详情

合成路线6

该中间体在本合成路线中的序号:(VI)

 

1 Wu GZ. Chen X,Wong YS et al.1999.3-hydroxy gamma-lactone based enaptiolelective synthesis of azetidinones. US 5886171
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 20651 N-[(E)-[4-(benzyloxy)phenyl]methylidene]-4-fluoroaniline; N-[(E)-[4-(benzyloxy)phenyl]methylidene]-N-(4-fluorophenyl)amine C20H16FNO 详情 详情
(II) 37681 (4S)-4-hydroxydihydro-2(3H)-furanone; (S)-3-Hydroxy-gamma-butyrolactone 7331-52-4 C4H6O3 详情 详情
(III) 20653 3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidinyl]propionic acid C25H22FNO4 详情 详情
(IV) 37683 (2S,3S)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxo-3-azetidinecarbaldehyde C23H18FNO3 详情 详情
(V) 37685 [[1-(4-fluorophenyl)vinyl]oxy](trimethyl)silane; 1-(4-fluorophenyl)vinyl trimethylsilyl ether C11H15FOSi 详情 详情
(VI) 20656 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-2-azetidinone C31H25F2NO3 详情 详情
(VII) 37688 (3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-4-(4-hydroxyphenyl)-2-azetidinone C24H19F2NO3 详情 详情
(VIII) 20631 (R)-Methyl oxazaborolidine; (3aR)-1-methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole 112022-83-0 C18H20BNO 详情 详情

合成路线7

该中间体在本合成路线中的序号:(I)

 

1 Wu GZ, Chen X,Wong YS et a1.1999. 3-hydroxy gamma-lactone based enantioselective synthesis of azetidinones. US 5886171
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 20656 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-2-azetidinone C31H25F2NO3 详情 详情
(II) 20656 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-2-azetidinone C31H25F2NO3 详情 详情
(III) 20631 (R)-Methyl oxazaborolidine; (3aR)-1-methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole 112022-83-0 C18H20BNO 详情 详情
(IV) 20657 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-2-azetidinone C31H27F2NO3 详情 详情

合成路线8

该中间体在本合成路线中的序号:(II)

 

1 Wu GZ, Chen X,Wong YS et a1.1999. 3-hydroxy gamma-lactone based enantioselective synthesis of azetidinones. US 5886171
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 20656 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-2-azetidinone C31H25F2NO3 详情 详情
(II) 20656 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-2-azetidinone C31H25F2NO3 详情 详情
(III) 20631 (R)-Methyl oxazaborolidine; (3aR)-1-methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole 112022-83-0 C18H20BNO 详情 详情
(IV) 20657 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-2-azetidinone C31H27F2NO3 详情 详情
Extended Information