Lhk8YF9ZU9

Base Information

• Chemical Name: Lhk8YF9ZU9
• CAS No.: 90822-22-3
• Molecular Formula: C₂₃H₃₄N₂O₇Si
• Molecular Weight: 478.618
• UNII: LHK8YF9ZU9
• Mol file: 90822-22-3.mol

Synonyms:90822-22-3;LHK8YF9ZU9;SCHEMBL9797065;4-Nitrobenzyl (R)-4-[(2R,3S)-3-[(R)-1-[(tert-Butyldimethylsilyl)oxy]ethyl]-4-oxo-2-azetidinyl]-3-oxopentanoate;(4-Nitrophenyl)methyl (gammaR,2R,3S)-3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-gamma-methyl-beta,4-dioxo-2-azetidinebutanoate;(R)-4-nitrobenzyl 4-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)-3-oxopentanoate;2-Azetidinebutanoic acid, 3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-gamma-methyl-beta,4-dioxo-, (4-nitrophenyl)methyl ester, (gammaR,2R,3S)-;2-Azetidinebutanoic acid, 3-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-gamma-methyl-beta,4-dioxo-, (4-nitrophenyl)methyl ester, [2R-[2alpha(R*),3beta(R*)]]-;4-Nitrobenzyl (R)-4-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)-3-oxopentanoate

Chemical Property of Lhk8YF9ZU9

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 478.21352796
• Heavy Atom Count: 33
• Complexity: 751

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C1C(NC1=O)C(C)C(=O)CC(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])O[Si](C)(C)C(C)(C)C
• Isomeric SMILES: C[C@H]([C@@H]1[C@H](NC1=O)[C@@H](C)C(=O)CC(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])O[Si](C)(C)C(C)(C)C

Technology Process of Lhk8YF9ZU9

There total 19 articles about Lhk8YF9ZU9 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:

magnesium mono-p-nitrobenzyl malonate (83972-01-4) + (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid (93711-85-4,97101-07-0,113033-46-8,120710-59-0,120710-60-3,90776-58-2) → (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one (90822-22-3)

Guidance literature:

(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid; With 1,1'-carbonyldiimidazole; In acetonitrile; at 20 ℃; for 0.5h;

magnesium mono-p-nitrobenzyl malonate; In acetonitrile; at 25 - 35 ℃; for 18h;

Reference yield:

(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid (93711-85-4,97101-07-0,113033-46-8,120710-59-0,120710-60-3,90776-58-2) + magnesium 4-nitrobenzyl malonate (105995-50-4) → (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one (90822-22-3)

Guidance literature:

With 1,1'-carbonyldiimidazole; In acetonitrile;

Reference yield:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) → (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one (90822-22-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) Sn(OSO₂CF₃)2, N-ethylpiperidine / 1) THF, -40 deg C, 2) THF, 0 deg C, 1 h

2: acetonitrile / 5.5 h / Ambient temperature

3: acetonitrile / 60 °C

With 1-ethyl-piperidine; tin(II) trifluoromethanesulfonate; In acetonitrile;

DOI:10.1021/jo00041a033

upstream raw materials:

magnesium 4-nitrobenzyl malonate

(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((R)-2-imidazol-1-yl-1-methyl-2-oxo-ethyl)-azetidin-2-one

(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(R)-2-(4,4-dimethyl-2-thioxo-oxazolidin-3-yl)-1-methyl-2-oxo-ethyl]-azetidin-2-one

(3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(R)-2-imidazol-1-yl-1-methyl-2-oxoethyl]azetidin-2-one

Downstream raw materials:

meropenem

(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]-heptane-2-carboxylate

p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate

Refernces

• 1、 -. "A PROCESS FOR THE PREPARATION OF THE INTERMEDIATE OF Β-METHYL CARBAPENEM". Page/Page column 13-14. . Retrieved 2010/11/28.
• 2、 Nagao, Yoshimitsu,Nagase, Yunosuke,Kumagai, Toshio,Matsunaga, Hiroshi,Abe, Takao,et al.. "β-Lactams. 3. Asymmetric Total Syntheis of New Non-Natural 1β-Methylcarbapenems Exhibiting Strong Antimicrobial Activities and Stability against Human Renal Dehydropeptidase-I". . p. 4243 - 4249. Retrieved 2007/10/02.