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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

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(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:
  • 4-AA
  • (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)-(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
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
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(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one Chemical Properties

Melting point:
107-109 °C(lit.)
alpha 
51 º (c=1, chloroform)
Boiling point:
358.3±27.0 °C(Predicted)
Density 
1.03±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
pka
12.86±0.60(Predicted)
optical activity
[α]20/D +51°, c = 1 in chloroform
InChIKey
GWHDKFODLYVMQG-UBHAPETDSA-N
CAS DataBase Reference
76855-69-1(CAS DataBase Reference)
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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

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

Chemical Properties

white 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 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.]

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