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(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one structure
(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one structure

(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
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. View more+
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
3.1 Density
1.039
3.1 Melting point
107-109℃
3.1 Boiling point
358.318°C at 760 mmHg
3.1 Refractive index
1.464
3.1 Flash Point
170.505°C
3.1 Precise Quality
287.15500
3.1 PSA
64.63000
3.1 logP
2.36070
3.1 Appearance
white to light yellow crystal powder
3.2 Chemical Properties
white to light yellow crystal powde
3.3 pKa
12.86±0.60(Predicted)
3.4 StorageTemp
2-8°C
3. Use and Manufacturing
4.1 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
4.2 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
5.1 Symbol
GHS07, GHS09
5.1 Hazard Codes
Xi
5.1 Signal Word
Warning
5.1 Risk Statements
R36;R43;R51/53
5.1 Safety Statements
S24;S26;S37;S61
5.1 Packing Group
III
5.1 Hazard Class
9
5.1 Hazard Declaration
H317-H319-H411
5.1 RIDADR
UN 3077
5.1 Caution Statement
P273-P280-P305 + P351 + P338
5.1 WGK Germany
2
5.1 Safety

Hazard Codes:??IrritantXiDangerousN
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:
  • 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
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(3s,4r)-4-acetoxy-3-[(r)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one CAS No.: 76855-69-1
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