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

CAS NO.：76855-69-1
Empirical Formula: C13H25NO4Si
Molecular Weight: 287.43
MDL number: MFCD00077636
EINECS: 408-050-9
SAFETY DATA SHEET (SDS)
Update Date: 2023-04-23 13:52:06

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

Chemical properties

white to light yellow crystal powde

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

(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.

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.]

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

Melting point:	107-109 °C(lit.)
Boiling point:	358.3±27.0 °C(Predicted)
alpha	51 º (c=1, chloroform)
Density	1.03±0.1 g/cm3(Predicted)
storage temp.	2-8°C
solubility	almost transparency in Methanol
form	powder to crystal
pka	12.86±0.60(Predicted)
color	White to Almost white
optical activity	[α]20/D +51°, c = 1 in chloroform
CAS DataBase Reference	76855-69-1(CAS DataBase Reference)

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

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07 Environment GHS09
GHS Hazard Statements	H317:Sensitisation, Skin H319:Serious eye damage/eye irritation H411:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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

InChIKey

GWHDKFODLYVMQG-UBHAPETDSA-N

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