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375845

Sigma-Aldrich

[3R(1′R,4R)]-(+)-4-Acetoxy-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone

98%

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About This Item

Empirical Formula (Hill Notation):
C13H25NO4Si
CAS Number:
76855-69-1
Molecular Weight:
287.43
EC Number:
408-050-9
MDL number:
MFCD00077636
UNSPSC Code:
12352005
PubChem Substance ID:
24863408
NACRES:
NA.22

Assay

98%

optical activity

[α]20/D +51°, c = 1 in chloroform

mp

107-109 °C (lit.)

storage temp.

2-8°C

SMILES string

C[C@@H](O[Si](C)(C)C(C)(C)C)C1[C@H](NC1=O)OC(C)=O

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-/m1/s1

InChI key

GWHDKFODLYVMQG-UBHAPETDSA-N

Related Categories

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H317,H319,H411

Hazard Classifications

Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Barbara Grzeszczyk et al.
The Journal of antibiotics, 66(3), 161-163 (2013-03-28)
A novel, practical and stereoselective synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone, a key intermediate in the preparation of β-lactam antibiotics is reported. The crucial step of the synthesis is based on the Cu(I)-mediated Kinugasa cycloaddition/rearrangement cascade between silyl protected (R)-3-butyn-2-ol and the nitrone

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