(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
- Iupac Name：[(2S,3R)-3-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate
- CAS No.: 76855-69-1
- Molecular Weight：287.431
- Modify Date.: 2022-11-07 12:08
- Introduction: (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one is an acetoxyazetidinone derivative used as an intermediate in the preparation of carbapenem antibiotics.
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1. Names and Identifiers
- 1.1 Name
- (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
- 1.2 Synonyms
(2R,3R)-3-[(1R)-1-{[Dimethyl(2-methyl-2-propanyl)silyl]oxy}ethyl]-4-oxo-2-azetidinyl acetate (2R,3R)-3-[(1R)-1-{[tert-Butyl(dimethyl)silyl]oxy}ethyl]-4-oxoazetidin-2-yl acetate (2R,3R)-3-[(1S)-1-{[Dimethyl(2-methyl-2-propanyl)silyl]oxy}ethyl]-4-oxo-2-azetidinyl acetate (2R,3R)-3-[(1S)-1-{[tert-Butyl(dimethyl)silyl]oxy}ethyl]-4-oxoazetidin-2-yl acetate (2R,3R)-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-4-OXOAZETIDIN-2-YLACETATE (3R,4R)-(+)-4-ACETOXY-3-[(R)-(T-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE (3R,4R)-4-(ACETYLOXY)-3-[(1R)-1-[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]ETHYL]-2-AZETIDINONE (3R,4R)-4-ACETOXY-3-[(R)-(T-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE (3R,4R)-4-ACETOXY-3-[(R)-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE (3R,4R)-4-ACETOXY-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL ]AZETIDIN-2-ONE (3R,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone [3R(1'R,4R)]-(+)-4-ACETOXY-3-[1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE 2-Azetidinone, 4-(acetyloxy)-3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-, (3R,4R)- 2-Azetidinone, 4-(acetyloxy)-3-[(1S)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-, (3R,4R)- 4-AA AOSA(4-AA) EINECS 408-050-9 MFCD00077636
- 1.3 CAS No.
- 76855-69-1
- 1.4 CID
- 13073897
- 1.5 EINECS(EC#)
- 408-050-9
- 1.6 Molecular Formula
- C13H25NO4Si (isomer)
- 1.7 Inchi
- InChI=1S/C13H25NO4Si/c1-8(18-19(6,7)13(3,4)5)10-11(16)14-12(10)17-9(2)15/h8,10,12H,1-7H3,(H,14,16)/t8-,10-,12-/m0/s1
- 1.8 InChkey
- GWHDKFODLYVMQG-PEXQALLHSA-N
- 1.9 Canonical Smiles
- CC(C1C(NC1=O)OC(=O)C)O[Si](C)(C)C(C)(C)C
- 1.10 Isomers Smiles
- C[C@@H]([C@@H]1[C@@H](NC1=O)OC(=O)C)O[Si](C)(C)C(C)(C)C
2. Properties
- 2.1 Density
- 1.039
- 2.1 Melting point
- 107-109℃
- 2.1 Boiling point
- 358.318°C at 760 mmHg
- 2.1 Refractive index
- 1.464
- 2.1 Flash Point
- 170.505°C
- 2.1 Precise Quality
- 287.15500
- 2.1 PSA
- 64.63000
- 2.1 logP
- 2.36070
- 2.1 Appearance
- white to light yellow crystal powder
- 2.2 Chemical Properties
- white to light yellow crystal powde
- 2.3 pKa
- 12.86±0.60(Predicted)
- 2.4 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 Purification Methods
- Purify it by chromatography on silica gel (3 x 14cm) for 50g of ester using 20% EtOAc in n-hexane. The eluate is evaporated, and the residue is recrystallised from hexane (white fluffy crystals). [Leanza et al. Tetrahedron 39 2505 1983.] (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one Preparation Products And Raw materials Raw materials
- 3.2 Usage
- (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one is an acetoxyazetidinone derivative used as an intermediate in the preparation of carbapenem antibiotics.
4. Safety and Handling
- 4.1 Symbol
- GHS07, GHS09
- 4.1 Hazard Codes
- Xi
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R36;R43;R51/53
- 4.1 Safety Statements
- S24;S26;S37;S61
- 4.1 Packing Group
- III
- 4.1 Hazard Class
- 9
- 4.1 Hazard Declaration
- H317-H319-H411
- 4.1 RIDADR
- UN 3077
- 4.1 Caution Statement
- P273-P280-P305 + P351 + P338
- 4.1 WGK Germany
- 2
- 4.1 Safety
-
Hazard Codes:??
Xi
N
Risk Statements?:
?R36:Irritating to eyes.
?R43:May cause sensitization by skin contact.
?R51/53 :Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements? :
?S24:Avoid contact with skin.
?S26:In case of contact with eyes, rinse immediately with plenty of WATER and seek medical advice.
?S37:Wear suitable gloves.
?S61 :Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR?: UN 3077 9/PG 3
WGK Germany? :2
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin sensitization, Category 1
Eye irritation, Category 2
Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |   |
| Signal word | Warning |
| Hazard statement(s) | H317 May cause an allergic skin reaction H319 Causes serious eye irritation H411 Toxic to aquatic life with long lasting effects |
| Precautionary statement(s) | |
| Prevention | P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P264 Wash ... thoroughly after handling. P273 Avoid release to the environment. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P391 Collect spillage. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Other Information
- 7.0 Chemical Properties
- white to light yellow crystal powde
- 7.1 Uses
- (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one is an acetoxyazetidinone derivative used as an intermediate in the preparation of carbapenem antibiotics.
- 7.2 Purification Methods
- Purify it by chromatography on silica gel (3 x 14cm) for 50g of ester using 20% EtOAc in n-hexane. The eluate is evaporated, and the residue is recrystallised from hexane (white fluffy crystals). [Leanza et al. Tetrahedron 39 2505 1983.]
8. Computational chemical data
- Molecular Weight: 287.431g/mol
- Molecular Formula: C13H25NO4Si
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 287.15528481
- Monoisotopic Mass: 287.15528481
- Complexity: 375
- Rotatable Bond Count: 6
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 4
- Topological Polar Surface Area: 64.6
- Heavy Atom Count: 19
- Defined Atom Stereocenter Count: 3
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADceByOAgAAAAAAAAAAAAAAABYAAAAAAAAAAAAAAAAAAAAAAAAHhAQAEAADRThoAZCCALABAEIAAGQGAAAAAAAAAAAAIEIAAEAABwAgAAOAAAHNgAAAAAAAAAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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10. Realated Product Infomation
![(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one structure](http://structimg.guidechem.com/6/30/27329.png)
-120YR
![(3R,4R)-4-Acetoxy-3-[(R)-(tert-butyldimethylsilyloxy)ethyl]- 2-azetidinone](https://structimg.guidechem.com/3/15/1647854.png)
![N-[2-(tert-ButyldiMethylsilyloxy)ethyl]MethylaMine](https://structimg.guidechem.com/5/5/1592404.png)
![(3R,4R)-4-Benzoyloxy-3-(1-tert-butyldimethlsilyloxy]ethyl)azetidin-2-one](https://structimg.guidechem.com/8/8/112927.png)
skype
![13C NMR : Predict (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one 76855-69-1](https://imgen1.guidechem.com/img/tupu/new/1495414497341138.png)
![1H NMR : Predict (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one 76855-69-1](https://imgen1.guidechem.com/img/tupu/new/1495414497401652.png)
![Predict 1H proton NMR (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one 76855-69-1](https://imgen1.guidechem.com/img/tupu/new/1495414495620882.png)
![IR : KBr disc (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one 76855-69-1](https://imgen1.guidechem.com/img/tupu/new/1495414499664951.png)
![IR : nujol mull (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one 76855-69-1](https://imgen1.guidechem.com/img/tupu/new/1495414501191662.png)
![Mass (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one 76855-69-1](https://imgen1.guidechem.com/img/tupu/new/1495414500085303.png)
