ChemicalBook Product Catalog Chemical Reagents Organic reagents Siloxane (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

(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one Basic information
Product Name:(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
Synonyms:(3s,4r)-4-acetoxy-3-[(r)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one;(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-(ACETYLOXY)-3-[(1R)-1-[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]ETHYL]-2-AZETIDINONE;[3R(1'R,4R)]-(+)-4-ACETOXY-3-[1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE;(2R,3R)-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-4-OXOAZETIDIN-2-YLACETATE;4-AOSA;(3R,4R)-4-acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone
CAS:76855-69-1
MF:C13H25NO4Si
MW:287.43
EINECS:408-050-9
Product Categories:Aliphatics;Intermediates & Fine Chemicals;Pharmaceuticals;Amides (Chiral);Azetidines;Chiral Building Blocks;Monoalkoxysilanes;Si (Classes of Silicon Compounds);Simple 4-Membered Ring Compounds;Si-O Compounds;Synthetic Organic Chemistry;Chiral Building Blocks;Lactams;Organic Building Blocks;(intermediate of imipenem);Chiral Compound
Mol File:76855-69-1.mol
(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 Chemical Properties
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
pka12.86±0.60(Predicted)
form powder to crystal
color White to Almost white
optical activity[α]20/D +51°, c = 1 in chloroform
InChIKeyGWHDKFODLYVMQG-UBHAPETDSA-N
CAS DataBase Reference76855-69-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,N
Risk Statements 36-43-51/53
Safety Statements 24-26-37-61
RIDADR UN 3077 9/PG 3
WGK Germany 2
HazardClass 9
PackingGroup III
HS Code 29337900
MSDS Information
ProviderLanguage
SigmaAldrich English
(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powde
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.
Purification MethodsPurify 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.]
T-BUTYLDIMETHYLSILANE (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one ISOPROPOXYTRIMETHYLSILANE Sodium triacetoxyborohydride TERT-BUTYLDIMETHYLSILANOL 4-ACETOXYAZETIDINONE(3S,4R)-4-ACETOXY-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]AZETIDIN-2-ONE (AZETIDIN-3-YL)METHANOL Acetoxy Cyclobutanone Diltiazem hydrochloride 3-(T-BUTYLDIMETHYLSILOXY)PROPANOL Meropenem 3-[(TERT-BUTYLDIMETHYLSILYL)OXY]-1-PROPANAL 4-Acetoxy-2-azetidinone 2-Azetidinone Benzyloxyacetyl chloride Laurocapram (3R,4R)-4-ACETOXY-3-[(3R)-1-(BUTYLDIMETHYL-SILYOXY)-ETHYL]-2-AZETIDIONE
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