[3-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]-4-oxo-azetidin-2-yl] benzoate

Base Information

• Chemical Name: [3-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]-4-oxo-azetidin-2-yl] benzoate
• CAS No.: 94944-10-2
• Molecular Formula: C18H27NO4Si
• Molecular Weight: 349.502
• DSSTox Substance ID: DTXSID90596866
• Mol file: 94944-10-2.mol

Synonyms:[3-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxo-azetidin-2-yl] benzoate;[3-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] benzoate;DTXSID90596866;A845137;3-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-4-oxoazetidin-2-yl benzoate

Chemical Property of [3-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]-4-oxo-azetidin-2-yl] benzoate

Chemical Property:

• PSA: 64.63000
• LogP: 3.65460
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 349.17093488
• Heavy Atom Count: 24
• Complexity: 466

Purity/Quality:

97% ^*data from raw suppliers

4-Benzoyloxy-2-azetidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCCC1C(NC1=O)OC(=O)C2=CC=CC=C2

Technology Process of [3-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]-4-oxo-azetidin-2-yl] benzoate

There total 7 articles about [3-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]-4-oxo-azetidin-2-yl] benzoate 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: 93.0%

[3S-[3α(S*),4β]]-4-benzoyl-3-[1-[[[(1,1-dimethyl-ethyl)dimethyl]silyl]oxy]ethyl]-2-azetidinone (94944-09-9) → 2-(2,3-Epoxy-propyl)-cyclohexanon (90611-54-4) + (3R,4R)-4-benzoyloxy-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one (94944-10-2)

Guidance literature:

With oxygen; benzaldehyde; iron(III) oxide; In benzene; under 760 Torr; Ambient temperature;

DOI:10.1016/S0040-4039(00)60823-7

Reference yield: 89.0%

[3S-[3α(S*),4β]]-4-benzoyl-3-[1-[[[(1,1-dimethyl-ethyl)dimethyl]silyl]oxy]ethyl]-2-azetidinone (94944-09-9) → (3R,4R)-4-benzoyloxy-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one (94944-10-2)

Guidance literature:

With monoperoxyphthalic acid; In ethyl acetate; for 18h;

DOI:10.1021/ja00291a069

Reference yield: 54.0%

Perbenzoic acid (93-59-4) + (3S,4S)-3-<(R)-1'-(dimethyl-t-butylsilyloxy)ethyl>-4-oxoazetidine-2-carboxylic acid (85253-97-0) → (3R,4R)-4-benzoyloxy-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one (94944-10-2)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1055/s-1990-26983

upstream raw materials:

Perbenzoic acid

(3S,4S)-3-<(R)-1'-(dimethyl-t-butylsilyloxy)ethyl>-4-oxoazetidine-2-carboxylic acid

[3S-[3α(S*),4β]]-4-benzoyl-3-[1-[[[(1,1-dimethyl-ethyl)dimethyl]silyl]oxy]ethyl]-2-azetidinone

(3S,4S)-4-Benzoyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-azetidin-2-one

Downstream raw materials:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

(5R)-selenapenem

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-butylsulfanyl-4-oxo-azetidin-1-yl}-acetic acid 4-nitro-benzyl ester

(E)-2-[(2S,3S)-2-Chloro-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-1-yl]-3-methanesulfonyloxy-but-2-enoic acid 4-nitro-benzyl ester

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